36:
375:
242:
577:
45:
27:
689:
975:. The lignin is degraded and becomes more watersoluble and thereby more easy to wash away from the pulp, while the anthraquinone is regenerated. This process gives an increase in yield of pulp, typically 1â3% and a reduction in
585:
987:
9,10-anthraquinone is used as a bird repellant on seeds, and as a gas generator in satellite balloons. It has also been mixed with lanolin and used as a wool spray to protect sheep flocks against
557:
2376:
4591:
999:
Several other isomers of anthraquinone exist, including the 1,2-, 1,4-, and 2,6-anthraquinones. They are of minor importance compared to 9,10-anthraquinone.
1307:
702:
3707:
3652:
1145:
1103:
4420:
3762:
3912:
2546:
4641:
1361:"A Novel Complex Locus UGT1 Encodes Human Bilirubin, Phenol, and other UDP-Glucuronosyltransferase Isozymes with Identical Carboxyl Termini"
4415:
2241:
414:
3517:
1438:
4087:
3287:
2031:
909:. Sulfonation with sulfuric acid gives anthroquinone-1-sulfonic acid, which reacts with sodium chlorate to give 1-chloroanthaquinone.
4252:
4182:
4162:
3657:
2824:
2286:
2705:
2261:
1474:
4007:
4485:
4435:
2839:
3942:
4581:
4390:
4047:
4027:
3987:
2794:
1737:
1127:
1074:
4576:
4506:
4405:
4062:
3917:
3547:
3392:
3002:
2629:
2406:
4656:
4440:
3752:
3242:
2917:
697:
3462:
4651:
4365:
4227:
4017:
3982:
1162:
809:
near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral
4541:
4480:
4012:
3927:
3897:
3877:
3742:
3737:
3112:
3037:
2680:
2634:
2501:
1762:
1291:
1087:
389:
147:
4646:
4606:
4556:
4232:
4032:
3782:
3712:
2201:
1772:
3847:
2740:
2461:
709:
4400:
4242:
4112:
4107:
3922:
3397:
3307:
2897:
2829:
2720:
2296:
2051:
1976:
1431:
4157:
881:
to give a 1,3-diphenylbutene, which then can be transformed to the anthraquinone. This process was pioneered by
4686:
4571:
4470:
4410:
4057:
3852:
3812:
3787:
3697:
3157:
2191:
2121:
1757:
1687:
890:
538:
3277:
1311:
4676:
4262:
4152:
3772:
3497:
3282:
3227:
3072:
3032:
2864:
2619:
2336:
2186:
1333:
4636:
4197:
3642:
4671:
4586:
4561:
4536:
4521:
4445:
4360:
4257:
4217:
4082:
4037:
3802:
3347:
3332:
3197:
2987:
2655:
2411:
2091:
2066:
2036:
1627:
1282:
Sturgeoff, L. G.; Pitl, Y. (1997) . "Low Kappa
Pulping without Capital Investment". In Goyal, G. C. (ed.).
613:
322:
237:
4621:
4566:
4511:
4222:
4142:
4042:
3757:
3722:
3567:
3457:
3172:
3167:
2992:
2952:
2849:
2660:
2624:
2476:
2466:
2321:
2181:
2041:
1991:
1986:
1961:
1921:
1867:
1632:
1622:
1597:
353:
576:
199:
4596:
4297:
4102:
3537:
3422:
3102:
3077:
3017:
2874:
2609:
2316:
2096:
2061:
1966:
1657:
1592:
1424:
1111:
623:
3887:
2151:
4696:
4601:
4455:
4335:
4307:
4277:
4192:
4122:
4077:
4052:
3972:
3872:
3832:
3527:
3147:
3137:
3062:
2586:
2446:
2441:
2421:
2106:
1903:
1882:
1842:
1767:
1359:
Ritter, J. K.; Chen, F.; Sheen, Y. Y.; Tran, H. M.; Kimura, S.; Yeatman, M. T.; Owens, I. S. (1992).
1587:
4661:
4551:
4531:
4395:
4237:
4147:
4117:
4097:
3992:
3947:
3777:
3687:
3617:
3502:
3492:
3322:
2879:
2819:
2784:
2591:
2571:
2531:
2306:
2176:
2141:
2101:
1852:
1692:
1682:
1612:
968:
956:
902:
370:
4127:
4735:
4631:
4490:
4340:
4282:
4207:
4187:
3907:
3857:
3717:
3682:
3622:
3552:
3107:
2854:
2834:
2566:
2486:
2381:
2341:
2311:
2246:
2131:
2116:
2026:
2016:
1677:
1602:
1557:
1411:
1406:
967:, and thereby protecting it from alkaline degradation (peeling). The anthraquinone is reduced to
837:
1892:
4370:
4092:
3842:
3822:
3797:
3747:
3662:
3637:
3592:
3562:
3542:
3512:
3477:
3432:
3407:
3382:
3267:
3192:
2972:
2665:
2601:
2401:
2126:
2046:
1732:
1707:
1484:
1479:
855:. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for producing substituted
4706:
4292:
4247:
3962:
3932:
3902:
3837:
3817:
3732:
3727:
3692:
3647:
3632:
3627:
3607:
3597:
3532:
3522:
3452:
3402:
2922:
2725:
2301:
2256:
2086:
2076:
1822:
1747:
1542:
1504:
599:
569:
1752:
4475:
4425:
4375:
4355:
4345:
4202:
4177:
3892:
3882:
3767:
3582:
3577:
3507:
3292:
3092:
3052:
2982:
2947:
2902:
2869:
2735:
2710:
2690:
2511:
2471:
2431:
2396:
2326:
2081:
1951:
1926:
1464:
1045:
863:
733:
331:
57:
219:
8:
4681:
4666:
4312:
4287:
4272:
4267:
3997:
3952:
3937:
3827:
3807:
3702:
3587:
3572:
3417:
3362:
3352:
3317:
3082:
2957:
2932:
2844:
2700:
2685:
2670:
2491:
2436:
2206:
2056:
2001:
1872:
1787:
1647:
1572:
959:(SET). The anthraquinone oxidizes the reducing end of polysaccharides in the pulp, i.e.,
631:
113:
4691:
3342:
2526:
1717:
374:
241:
179:
123:
35:
4430:
4380:
4350:
4212:
4002:
3792:
3677:
3612:
3602:
3367:
3297:
3262:
3257:
3237:
3232:
3177:
3087:
2937:
2799:
2789:
2695:
2481:
2426:
2356:
2276:
2171:
2071:
2006:
1931:
1777:
1642:
1577:
1562:
1008:
845:
790:
159:
1380:
4167:
3487:
3372:
3337:
3302:
3247:
3202:
3117:
3097:
3047:
3042:
3012:
2997:
2907:
2814:
2750:
2715:
2541:
2416:
2291:
2216:
2196:
2111:
1946:
1941:
1887:
1797:
1702:
1662:
1617:
1499:
1494:
1459:
1385:
1287:
1158:
1123:
1083:
1017:
In terms of metabolism of substituted anthraquinones, the enzyme encoded by the gene
3162:
4701:
4546:
4516:
4460:
4385:
4317:
4072:
4022:
3867:
3672:
3447:
3442:
3387:
3377:
3152:
2962:
2942:
2912:
2809:
2745:
2730:
2561:
2516:
2506:
2496:
2391:
2371:
2366:
2351:
2346:
2226:
2221:
2161:
2146:
2136:
1981:
1971:
1837:
1827:
1727:
1722:
1697:
1637:
1489:
1448:
1375:
1264:
1241:
1214:
1187:
1150:
1115:
736:
521:
437:
1817:
4611:
4302:
4137:
4132:
3427:
3412:
3357:
3312:
3272:
3222:
3187:
3182:
3127:
3122:
3057:
3007:
2927:
2755:
2639:
2614:
2576:
2551:
2536:
2521:
2456:
2331:
2281:
2271:
2251:
2211:
2021:
2011:
1996:
1792:
1712:
1582:
1552:
1537:
1532:
1360:
1108:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
1102:
941:
295:
250:
4616:
4526:
4465:
3557:
3467:
3437:
3212:
3067:
2804:
2581:
2451:
2266:
2236:
1936:
1832:
1607:
1469:
1035:
918:
867:
856:
786:
680:
1416:
4729:
4626:
4327:
4172:
4067:
3862:
3252:
3217:
3207:
3142:
3132:
3022:
2859:
2675:
2386:
2361:
2231:
1877:
1862:
1847:
1742:
1672:
1652:
1567:
1261:
A comprehensive mechanism for anthraquinone mass transfer in alkaline pulping
1245:
1218:
1205:
Scott, W. J.; Allen, C. F. H. (1938). "Potassium
Anthraquinone-α-Sulfonate".
1191:
1154:
964:
937:
781:
groups are located on the central ring. It is used as a digester additive to
510:
500:
230:
1358:
821:
There are several current industrial methods to produce 9,10-anthraquinone:
627:
3667:
3027:
2779:
2556:
2156:
1956:
1807:
1802:
1667:
1522:
1030:
976:
945:
929:
830:
782:
1389:
1119:
1021:
has glucuronidase activity with many substrates including anthraquinones.
805:
but soluble in hot organic solvents. It is almost completely insoluble in
2166:
1812:
1782:
1547:
1407:
National
Pollutant Inventory â Polycyclic Aromatic Hydrocarbon Fact Sheet
646:
4450:
3977:
3327:
826:
798:
671:
465:
210:
44:
1268:
398:
InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
1079:
960:
871:
794:
619:
342:
26:
679:
Except where otherwise noted, data are given for materials in their
1857:
1527:
1040:
952:
928:
9,10-Anthraquinone is used as a digester additive in production of
906:
270:
789:
are generated by organisms or synthesised industrially for use as
639:
146:
1517:
878:
841:
810:
806:
666:
486:
282:
1232:
Scott, W. J.; Allen, C. F. H. (1938). "α-Chloroanthraquinone".
1018:
972:
933:
778:
770:
190:
797:. Anthraquinone is a yellow, highly crystalline solid, poorly
949:
849:
802:
774:
306:
170:
136:
358:
882:
773:
exist but these terms usually refer to 9,10-anthraquinone (
261:
988:
1178:
Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone".
1263:(Thesis). Georgia Institute of Technology. p. 30.
16:
Yellow chemical compound: building block of many dyes
4592:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
923:
905:(anthrahydroquinone). Reduction with copper gives
3653:Divinylcyclopropane-cycloheptadiene rearrangement
1104:International Union of Pure and Applied Chemistry
889:It also arises via the RickertâAlder reaction, a
4727:
1014:, probably because it is so insoluble in water.
294:
1446:
122:
3913:Thermal rearrangement of aromatic hydrocarbons
2547:Thermal rearrangement of aromatic hydrocarbons
1412:Molecules Spontaneously Form Honeycomb Network
1146:Ullmann's Encyclopedia of Industrial Chemistry
635:
605:
4642:Lectka enantioselective beta-lactam synthesis
1902:
1432:
1281:
4421:Inverse electron-demand DielsâAlder reaction
2242:Heterogeneous metal catalyzed cross-coupling
1177:
505:284.8 °C (544.6 °F; 558.0 K)
3763:Lobry de BruynâVan Ekenstein transformation
1352:
1439:
1425:
1231:
1204:
373:
240:
218:
4253:Petrenko-Kritschenko piperidone synthesis
3708:FritschâButtenbergâWiechell rearrangement
1379:
330:
4416:Intramolecular DielsâAlder cycloaddition
1331:
369:
4728:
4436:Metal-centered cycloaddition reactions
4088:DebusâRadziszewski imidazole synthesis
2032:BodrouxâChichibabin aldehyde synthesis
1136:
874:followed by oxidative dehydrogenation.
651:185 °C (365 °F; 458 K)
515:377 °C (711 °F; 650 K)
231:
4582:Diazoalkane 1,3-dipolar cycloaddition
4486:Vinylcyclopropane (5+2) cycloaddition
4391:Diazoalkane 1,3-dipolar cycloaddition
4163:HurdâMori 1,2,3-thiadiazole synthesis
3658:DowdâBeckwith ring-expansion reaction
2825:HurdâMori 1,2,3-thiadiazole synthesis
1901:
1738:LFER solvent coefficients (data page)
1420:
1142:
1075:CRC Handbook of Chemistry and Physics
1067:
1065:
1063:
1061:
955:. The reaction mechanism may involve
401:Key: RZVHIXYEVGDQDX-UHFFFAOYSA-N
198:
178:
3393:Sharpless asymmetric dihydroxylation
2630:Methoxymethylenetriphenylphosphorane
1258:
777:: 9,10-dioxoanthracene) wherein the
3518:AllenâMillarâTrippett rearrangement
1334:"How to solve a problem like a kea"
877:The acid-catalyzed dimerization of
285:
269:
13:
4657:Nitrone-olefin (3+2) cycloaddition
4652:Niementowski quinazoline synthesis
4441:Nitrone-olefin (3+2) cycloaddition
4366:Azide-alkyne Huisgen cycloaddition
4228:Niementowski quinazoline synthesis
3983:Azide-alkyne Huisgen cycloaddition
3288:MeerweinâPonndorfâVerley reduction
2840:LeimgruberâBatcho indole synthesis
1058:
948:processes. The anthraquinone is a
14:
4747:
4481:Trimethylenemethane cycloaddition
4183:JohnsonâCoreyâChaykovsky reaction
4048:CadoganâSundberg indole synthesis
4028:BohlmannâRahtz pyridine synthesis
3988:BaeyerâEmmerling indole synthesis
2795:CadoganâSundberg indole synthesis
2287:JohnsonâCoreyâChaykovsky reaction
1400:
89:9,10-Dihydro-9,10-dioxoanthracene
4577:CookâHeilbron thiazole synthesis
4406:Hexadehydro DielsâAlder reaction
4233:Niementowski quinoline synthesis
4063:CookâHeilbron thiazole synthesis
4008:BischlerâMöhlau indole synthesis
3918:TiffeneauâDemjanov rearrangement
3548:BakerâVenkataraman rearrangement
2706:HornerâWadsworthâEmmons reaction
2377:Mizoroki-Heck vs. Reductive Heck
2262:HornerâWadsworthâEmmons reaction
1773:Neighbouring group participation
1072:Haynes, William M., ed. (2016).
994:
924:Digester additive in papermaking
687:
575:
449:
43:
34:
25:
4113:Fiesselmann thiophene synthesis
3943:WestphalenâLettrĂ© rearrangement
3923:Vinylcyclopropane rearrangement
3753:KornblumâDeLaMare rearrangement
3398:Epoxidation of allylic alcohols
3308:Noyori asymmetric hydrogenation
3243:KornblumâDeLaMare rearrangement
2918:GallagherâHollander degradation
1368:Journal of Biological Chemistry
1325:
912:
683:(at 25 °C , 100 kPa).
4572:Chichibabin pyridine synthesis
4058:Chichibabin pyridine synthesis
4018:BlumâIttah aziridine synthesis
3853:Ring expansion and contraction
2122:Cross dehydrogenative coupling
1332:Dudding, Adam (29 July 2012).
1300:
1275:
1252:
1225:
1198:
1171:
1112:The Royal Society of Chemistry
1096:
1007:Anthraquinone has no recorded
539:Occupational safety and health
455:
443:
1:
4542:BischlerâNapieralski reaction
4500:Heterocycle forming reactions
4153:Hemetsberger indole synthesis
4013:BischlerâNapieralski reaction
3928:WagnerâMeerwein rearrangement
3898:SommeletâHauser rearrangement
3878:SeyferthâGilbert homologation
3743:IrelandâClaisen rearrangement
3738:HofmannâMartius rearrangement
3498:2,3-sigmatropic rearrangement
3113:CoreyâWinter olefin synthesis
3038:BartonâMcCombie deoxygenation
2681:CoreyâWinter olefin synthesis
2635:SeyferthâGilbert homologation
2502:SeyferthâGilbert homologation
1381:10.1016/S0021-9258(19)50724-4
1286:. TAPPI Press. pp. 3â9.
1051:
982:
4647:LehmstedtâTanasescu reaction
4607:GabrielâColman rearrangement
4562:Bucherer carbazole synthesis
4557:BorscheâDrechsel cyclization
4537:Bernthsen acridine synthesis
4522:Bamberger triazine synthesis
4507:AlgarâFlynnâOyamada reaction
4218:Nazarov cyclization reaction
4083:De Kimpe aziridine synthesis
4038:Bucherer carbazole synthesis
4033:BorscheâDrechsel cyclization
3803:Nazarov cyclization reaction
3783:MeyerâSchuster rearrangement
3713:GabrielâColman rearrangement
3463:WolffensteinâBöters reaction
3348:Reduction of nitro compounds
3198:Grundmann aldehyde synthesis
3003:AlgarâFlynnâOyamada reaction
2412:Olefin conversion technology
2407:NozakiâHiyamaâKishi reaction
2202:GabrielâColman rearrangement
2092:Claisen-Schmidt condensation
2037:Bouveault aldehyde synthesis
896:
816:
7:
4622:Hantzsch pyridine synthesis
4401:Enoneâalkene cycloadditions
4223:Nenitzescu indole synthesis
4143:Hantzsch pyridine synthesis
4108:FerrarioâAckermann reaction
3758:Kowalski ester homologation
3723:Halogen dance rearrangement
3568:Benzilic acid rearrangement
2993:Akabori amino-acid reaction
2953:Von Braun amide degradation
2898:BarbierâWieland degradation
2850:Nenitzescu indole synthesis
2830:KharaschâSosnovsky reaction
2721:JuliaâKocienski olefination
2625:Kowalski ester homologation
2322:Kowalski ester homologation
2297:JuliaâKocienski olefination
2052:CadiotâChodkiewicz coupling
1977:Aza-BaylisâHillman reaction
1922:Acetoacetic ester synthesis
1633:Dynamic binding (chemistry)
1623:Conrotatory and disrotatory
1598:Charge remote fragmentation
1143:Vogel, A. "Anthraquinone".
1071:
1024:
10:
4752:
4687:RobinsonâGabriel synthesis
4637:Kröhnke pyridine synthesis
4471:Retro-DielsâAlder reaction
4411:Imine DielsâAlder reaction
4198:Kröhnke pyridine synthesis
3813:NewmanâKwart rearrangement
3788:MislowâEvans rearrangement
3698:FischerâHepp rearrangement
3643:Di-Ï-methane rearrangement
3423:Stephen aldehyde synthesis
3158:EschweilerâClarke reaction
2875:Williamson ether synthesis
2192:FujiwaraâMoritani reaction
2097:Combes quinoline synthesis
2062:Carbonyl olefin metathesis
1763:More O'FerrallâJencks plot
1688:GrunwaldâWinstein equation
1658:Electron-withdrawing group
1593:Catalytic resonance theory
1308:"www.americanheritage.com"
971:which then can react with
916:
891:retro-DielsâAlder reaction
422:O=C1c2ccccc2C(=O)c3ccccc13
4697:Urech hydantoin synthesis
4677:PomeranzâFritsch reaction
4602:Fischer oxazole synthesis
4499:
4336:1,3-Dipolar cycloaddition
4326:
4308:Urech hydantoin synthesis
4278:Reissert indole synthesis
4263:PomeranzâFritsch reaction
4193:Knorr quinoline synthesis
4123:Fischer oxazole synthesis
4053:Camps quinoline synthesis
3973:1,3-Dipolar cycloaddition
3961:
3873:Semipinacol rearrangement
3848:RambergâBĂ€cklund reaction
3833:Piancatelli rearrangement
3773:McFadyenâStevens reaction
3528:Alpha-ketol rearrangement
3476:
3283:McFadyenâStevens reaction
3228:KilianiâFischer synthesis
3148:Elbs persulfate oxidation
3073:BouveaultâBlanc reduction
3033:BaeyerâVilliger oxidation
2971:
2888:
2865:SchottenâBaumann reaction
2768:
2741:RambergâBĂ€cklund reaction
2648:
2620:KilianiâFischer synthesis
2600:
2462:RambergâBĂ€cklund reaction
2447:Pinacol coupling reaction
2442:Piancatelli rearrangement
2337:LiebeskindâSrogl coupling
2187:FujimotoâBelleau reaction
1910:
1904:List of organic reactions
1768:Negative hyperconjugation
1513:
1455:
1002:
787:anthraquinone derivatives
677:
655:
556:
536:
531:
430:
410:
385:
106:
68:
56:
51:
42:
33:
24:
4672:PictetâSpengler reaction
4587:EinhornâBrunner reaction
4552:Boger pyridine synthesis
4446:Oxo-DielsâAlder reaction
4361:Aza-DielsâAlder reaction
4258:PictetâSpengler reaction
4158:HofmannâLöffler reaction
4148:Hegedus indole synthesis
4118:Fischer indole synthesis
3993:Bartoli indole synthesis
3948:Willgerodt rearrangement
3778:McLafferty rearrangement
3688:Ferrier carbocyclization
3503:2,3-Wittig rearrangement
3493:1,2-Wittig rearrangement
3333:ParikhâDoering oxidation
3323:Oxygen rebound mechanism
2988:AdkinsâPeterson reaction
2880:Yamaguchi esterification
2820:Hegedus indole synthesis
2785:Bartoli indole synthesis
2656:BamfordâStevens reaction
2572:Weinreb ketone synthesis
2532:Stork enamine alkylation
2307:Knoevenagel condensation
2177:Ferrier carbocyclization
2067:CastroâStephens coupling
1693:Hammett acidity function
1683:Free-energy relationship
1628:CurtinâHammett principle
1613:Conformational isomerism
1246:10.15227/orgsyn.018.0015
1219:10.15227/orgsyn.018.0072
1192:10.15227/orgsyn.014.0004
1155:10.1002/14356007.a02_347
991:attacks in New Zealand.
969:9,10-dihydroxyanthracene
957:single electron transfer
614:Precautionary statements
4632:Knorr pyrrole synthesis
4567:BuchererâBergs reaction
4512:AllanâRobinson reaction
4491:Wagner-Jauregg reaction
4283:Ring-closing metathesis
4208:Larock indole synthesis
4188:Knorr pyrrole synthesis
4043:BuchererâBergs reaction
3908:Stieglitz rearrangement
3888:SkattebĂžl rearrangement
3858:Ring-closing metathesis
3718:Group transfer reaction
3683:Favorskii rearrangement
3623:Cornforth rearrangement
3553:Bamberger rearrangement
3458:WolffâKishner reduction
3278:MarkĂłâLam deoxygenation
3173:FlemingâTamao oxidation
3168:FischerâTropsch process
2855:Oxymercuration reaction
2835:Knorr pyrrole synthesis
2661:BartonâKellogg reaction
2567:Wagner-Jauregg reaction
2487:Ring-closing metathesis
2477:ReimerâTiemann reaction
2467:RauhutâCurrier reaction
2382:Nef isocyanide reaction
2342:Malonic ester synthesis
2312:Knorr pyrrole synthesis
2247:High dilution principle
2182:FriedelâCrafts reaction
2117:Cross-coupling reaction
2042:BuchererâBergs reaction
2027:Blanc chloromethylation
2017:Blaise ketone synthesis
1992:BaylisâHillman reaction
1987:BartonâKellogg reaction
1962:AllanâRobinson reaction
1868:WoodwardâHoffmann rules
1603:Charge-transfer complex
1149:. Weinheim: Wiley-VCH.
838:Friedel-Crafts reaction
833:is the typical oxidant.
793:, pharmaceuticals, and
86:Anthracene-9,10-quinone
4597:FeistâBenary synthesis
4371:Bradsher cycloaddition
4341:4+4 Photocycloaddition
4298:SimmonsâSmith reaction
4243:PaternĂČâBĂŒchi reaction
4103:FeistâBenary synthesis
4093:Dieckmann condensation
3843:Pummerer rearrangement
3823:Oxy-Cope rearrangement
3798:Myers allene synthesis
3748:Jacobsen rearrangement
3663:Electrocyclic reaction
3638:Demjanov rearrangement
3593:Buchner ring expansion
3563:Beckmann rearrangement
3543:Aza-Cope rearrangement
3538:ArndtâEistert reaction
3513:Alkyne zipper reaction
3433:Transfer hydrogenation
3408:Sharpless oxyamination
3383:Selenoxide elimination
3268:Lombardo methylenation
3193:Griesbaum coozonolysis
3103:CoreyâItsuno reduction
3078:BoylandâSims oxidation
3018:AngeliâRimini reaction
2666:Boord olefin synthesis
2610:ArndtâEistert reaction
2602:Homologation reactions
2402:Nitro-Mannich reaction
2317:KolbeâSchmitt reaction
2127:Cross-coupling partner
2047:Buchner ring expansion
1967:ArndtâEistert reaction
1733:Kinetic isotope effect
1480:Rearrangement reaction
785:for papermaking. Many
4456:PausonâKhand reaction
4293:Sharpless epoxidation
4248:Pechmann condensation
4128:FriedlÀnder synthesis
4078:DavisâBeirut reaction
3933:Wallach rearrangement
3903:Stevens rearrangement
3838:Pinacol rearrangement
3818:Overman rearrangement
3733:Hofmann rearrangement
3728:Hayashi rearrangement
3693:Ferrier rearrangement
3648:Dimroth rearrangement
3633:Curtius rearrangement
3628:Criegee rearrangement
3608:Claisen rearrangement
3598:Carroll rearrangement
3533:Amadori rearrangement
3523:Allylic rearrangement
3403:Sharpless epoxidation
3138:DessâMartin oxidation
3063:BohnâSchmidt reaction
2923:Hofmann rearrangement
2726:Kauffmann olefination
2649:Olefination reactions
2587:WurtzâFittig reaction
2422:PalladiumâNHC complex
2302:Kauffmann olefination
2257:Homologation reaction
2107:CoreyâHouse synthesis
2087:Claisen rearrangement
1883:YukawaâTsuno equation
1843:SwainâLupton equation
1823:Spherical aromaticity
1758:MöbiusâHĂŒckel concept
1543:Aromatic ring current
1505:Substitution reaction
1284:Anthraquinone Pulping
1120:10.1039/9781849733069
62:Anthracene-9,10-dione
4662:PaalâKnorr synthesis
4532:BartonâZard reaction
4476:Staudinger synthesis
4426:Ketene cycloaddition
4396:DielsâAlder reaction
4376:Cheletropic reaction
4356:Alkyne trimerisation
4238:PaalâKnorr synthesis
4203:Kulinkovich reaction
4178:Jacobsen epoxidation
4098:DielsâAlder reaction
3893:Smiles rearrangement
3883:Sigmatropic reaction
3768:Lossen rearrangement
3618:CoreyâFuchs reaction
3583:Boekelheide reaction
3578:Bergmann degradation
3508:Achmatowicz reaction
3293:Methionine sulfoxide
3093:Clemmensen reduction
3053:Bergmann degradation
2983:Acyloin condensation
2948:Strecker degradation
2903:Bergmann degradation
2870:Ullmann condensation
2736:Peterson olefination
2711:Hydrazone iodination
2691:Elimination reaction
2592:ZinckeâSuhl reaction
2512:Sonogashira coupling
2472:Reformatsky reaction
2432:Peterson olefination
2397:Nierenstein reaction
2327:Kulinkovich reaction
2142:DielsâAlder reaction
2102:CoreyâFuchs reaction
2082:Claisen condensation
1952:Alkyne trimerisation
1927:Acyloin condensation
1893:ÎŁ-bishomoaromaticity
1853:ThorpeâIngold effect
1465:Elimination reaction
1259:Samp, J. C. (2008).
1046:2-Ethylanthraquinone
936:processes, like the
903:dihydroanthraquinone
901:Hydrogenation gives
864:Diels-Alder reaction
552:possible carcinogen
77:9,10-Anthracenedione
58:Preferred IUPAC name
4682:Prilezhaev reaction
4667:Pellizzari reaction
4346:(4+3) cycloaddition
4313:Van Leusen reaction
4288:Robinson annulation
4273:Pschorr cyclization
4268:Prilezhaev reaction
3998:Bergman cyclization
3953:Wolff rearrangement
3938:Weerman degradation
3828:Pericyclic reaction
3808:Neber rearrangement
3703:Fries rearrangement
3588:Brook rearrangement
3573:Bergman cyclization
3418:Staudinger reaction
3363:Rosenmund reduction
3353:Reductive amination
3318:Oppenauer oxidation
3108:CoreyâKim oxidation
3083:Cannizzaro reaction
2958:Weerman degradation
2933:Isosaccharinic acid
2845:Mukaiyama hydration
2701:Hofmann elimination
2686:Dehydrohalogenation
2671:Chugaev elimination
2492:Robinson annulation
2437:Pfitzinger reaction
2207:Gattermann reaction
2152:WulffâDötz reaction
2132:DakinâWest reaction
2057:Carbonyl allylation
2002:Bergman cyclization
1788:Kennedy J. P. Orton
1708:Hammond's postulate
1678:FlippinâLodge angle
1648:Electromeric effect
1573:Beta-silicon effect
1558:BakerâNathan effect
522:Solubility in water
473: g·mol
160:Beilstein Reference
21:
20:9,10-Anthraquinone
4431:McCormack reaction
4381:Conia-ene reaction
4213:Madelung synthesis
4003:Biginelli reaction
3793:Mumm rearrangement
3678:Favorskii reaction
3613:Cope rearrangement
3603:Chan rearrangement
3368:Rubottom oxidation
3298:Miyaura borylation
3263:Lipid peroxidation
3258:Lindgren oxidation
3238:Kornblum oxidation
3233:Kolbe electrolysis
3178:Fukuyama reduction
3088:Carbonyl reduction
2938:Marker degradation
2800:Diazonium compound
2790:Boudouard reaction
2769:Carbon-heteroatom
2696:Grieco elimination
2482:Rieche formylation
2427:Passerini reaction
2357:Meerwein arylation
2277:Hydroxymethylation
2172:Favorskii reaction
2072:Chan rearrangement
2007:Biginelli reaction
1932:Aldol condensation
1778:2-Norbornyl cation
1753:Möbius aromaticity
1748:Markovnikov's rule
1643:Effective molarity
1588:BĂŒrgiâDunitz angle
1578:Bicycloaromaticity
846:phthalic anhydride
710:Infobox references
656:Related compounds
19:
4723:
4722:
4719:
4718:
4715:
4714:
4707:WohlâAue reaction
4351:6+4 Cycloaddition
4168:Iodolactonization
3488:1,2-rearrangement
3453:WohlâAue reaction
3373:Sabatier reaction
3338:Pinnick oxidation
3303:Mozingo reduction
3248:Leuckart reaction
3203:Haloform reaction
3118:Criegee oxidation
3098:Collins oxidation
3048:Benkeser reaction
3043:Bechamp reduction
3013:Andrussow process
2998:Alcohol oxidation
2908:Edman degradation
2815:Haloform reaction
2764:
2763:
2751:Takai olefination
2716:Julia olefination
2542:Takai olefination
2417:Olefin metathesis
2292:Julia olefination
2217:Grignard reaction
2197:Fukuyama coupling
2112:Coupling reaction
2077:ChanâLam coupling
1947:Alkyne metathesis
1942:Alkane metathesis
1798:Phosphaethynolate
1703:George S. Hammond
1663:Electronic effect
1618:Conjugated system
1500:Stereospecificity
1495:Stereoselectivity
1460:Addition reaction
1449:organic reactions
1338:Sunday Star Times
1234:Organic Syntheses
1207:Organic Syntheses
1180:Organic Syntheses
1129:978-0-85404-182-4
1078:(97th ed.).
825:The oxidation of
718:Chemical compound
716:
715:
662:Related compounds
600:Hazard statements
354:CompTox Dashboard
148:Interactive image
83:9,10-Anthrachinon
4743:
4702:Wenker synthesis
4692:Stollé synthesis
4547:Bobbitt reaction
4517:Auwers synthesis
4461:Povarov reaction
4386:Cyclopropanation
4324:
4323:
4318:Wenker synthesis
4073:Darzens reaction
4023:Bobbitt reaction
3868:Schmidt reaction
3673:Enyne metathesis
3448:Whiting reaction
3443:Wharton reaction
3388:Shapiro reaction
3378:Sarett oxidation
3343:Prévost reaction
3153:Emde degradation
2963:Wohl degradation
2943:Ruff degradation
2913:Emde degradation
2810:Grignard reagent
2746:Shapiro reaction
2731:McMurry reaction
2598:
2597:
2562:Ullmann reaction
2527:Stollé synthesis
2517:Stetter reaction
2507:Shapiro reaction
2497:Sakurai reaction
2392:Negishi coupling
2372:Minisci reaction
2367:Michael reaction
2352:McMurry reaction
2347:Mannich reaction
2227:Hammick reaction
2222:Grignard reagent
2162:Enyne metathesis
2147:Doebner reaction
2137:Darzens reaction
1982:Barbier reaction
1972:Auwers synthesis
1899:
1898:
1873:Woodward's rules
1838:Superaromaticity
1828:Spiroaromaticity
1728:Inductive effect
1723:Hyperconjugation
1698:Hammett equation
1638:Edwards equation
1490:Regioselectivity
1441:
1434:
1427:
1418:
1417:
1394:
1393:
1383:
1374:(5): 3257â3261.
1365:
1356:
1350:
1349:
1347:
1345:
1329:
1323:
1322:
1320:
1319:
1310:. Archived from
1304:
1298:
1297:
1279:
1273:
1272:
1256:
1250:
1249:
1229:
1223:
1222:
1202:
1196:
1195:
1175:
1169:
1168:
1140:
1134:
1133:
1100:
1094:
1093:
1082:. p. 3.28.
1069:
768:
767:
766:
758:
757:
749:
748:
737:organic compound
700:
694:
691:
690:
641:
637:
633:
629:
625:
621:
607:
579:
494:
472:
457:
451:
445:
438:Chemical formula
378:
377:
362:
360:
334:
298:
287:
273:
251:Gmelin Reference
244:
233:
222:
202:
182:
150:
126:
47:
38:
29:
22:
18:
4751:
4750:
4746:
4745:
4744:
4742:
4741:
4740:
4726:
4725:
4724:
4711:
4612:Gewald reaction
4495:
4322:
4303:Skraup reaction
4138:Graham reaction
4133:Gewald reaction
3964:
3957:
3479:
3472:
3428:Swern oxidation
3413:Stahl oxidation
3358:Riley oxidation
3313:Omega oxidation
3273:Luche reduction
3223:Jones oxidation
3188:Glycol cleavage
3183:Ganem oxidation
3128:Davis oxidation
3123:Dakin oxidation
3058:Birch reduction
3008:Amide reduction
2974:
2967:
2928:Hooker reaction
2890:
2884:
2772:
2770:
2760:
2756:Wittig reaction
2644:
2640:Wittig reaction
2615:Hooker reaction
2596:
2577:Wittig reaction
2552:Thorpe reaction
2537:Suzuki reaction
2522:Stille reaction
2457:Quelet reaction
2332:Kumada coupling
2282:Ivanov reaction
2272:Hydrovinylation
2252:Hiyama coupling
2212:Glaser coupling
2022:Blaise reaction
2012:Bingel reaction
1997:Benary reaction
1914:
1912:
1906:
1897:
1793:Passive binding
1713:Homoaromaticity
1563:Baldwin's rules
1538:Antiaromaticity
1533:Anomeric effect
1509:
1451:
1445:
1403:
1398:
1397:
1363:
1357:
1353:
1343:
1341:
1330:
1326:
1317:
1315:
1306:
1305:
1301:
1294:
1280:
1276:
1257:
1253:
1230:
1226:
1203:
1199:
1176:
1172:
1165:
1141:
1137:
1130:
1114:. p. 724.
1101:
1097:
1090:
1070:
1059:
1054:
1027:
1012:
1005:
997:
985:
940:, the alkaline
926:
921:
915:
899:
853:
848:in presence of
819:
765:
762:
761:
760:
756:
753:
752:
751:
747:
744:
743:
742:
740:
730:dioxoanthracene
726:anthracenedione
719:
712:
707:
706:
705: ?)
696:
692:
688:
684:
670:
663:
616:
602:
588:
572:
549:
524:
492:
470:
460:
454:
448:
440:
426:
423:
418:
417:
406:
403:
402:
399:
393:
392:
381:
363:
356:
337:
317:
301:
288:
276:
253:
225:
205:
185:
162:
153:
140:
129:
116:
102:
101:
64:
63:
17:
12:
11:
5:
4749:
4739:
4738:
4736:Anthraquinones
4721:
4720:
4717:
4716:
4713:
4712:
4710:
4709:
4704:
4699:
4694:
4689:
4684:
4679:
4674:
4669:
4664:
4659:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4617:Hantzsch ester
4614:
4609:
4604:
4599:
4594:
4589:
4584:
4579:
4574:
4569:
4564:
4559:
4554:
4549:
4544:
4539:
4534:
4529:
4527:Banert cascade
4524:
4519:
4514:
4509:
4503:
4501:
4497:
4496:
4494:
4493:
4488:
4483:
4478:
4473:
4468:
4466:Prato reaction
4463:
4458:
4453:
4448:
4443:
4438:
4433:
4428:
4423:
4418:
4413:
4408:
4403:
4398:
4393:
4388:
4383:
4378:
4373:
4368:
4363:
4358:
4353:
4348:
4343:
4338:
4332:
4330:
4321:
4320:
4315:
4310:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4225:
4220:
4215:
4210:
4205:
4200:
4195:
4190:
4185:
4180:
4175:
4170:
4165:
4160:
4155:
4150:
4145:
4140:
4135:
4130:
4125:
4120:
4115:
4110:
4105:
4100:
4095:
4090:
4085:
4080:
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3985:
3980:
3975:
3969:
3967:
3959:
3958:
3956:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3905:
3900:
3895:
3890:
3885:
3880:
3875:
3870:
3865:
3860:
3855:
3850:
3845:
3840:
3835:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3730:
3725:
3720:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3558:Banert cascade
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3484:
3482:
3478:Rearrangement
3474:
3473:
3471:
3470:
3468:Zinin reaction
3465:
3460:
3455:
3450:
3445:
3440:
3438:Wacker process
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3245:
3240:
3235:
3230:
3225:
3220:
3215:
3213:Hydrogenolysis
3210:
3205:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3163:Ătard reaction
3160:
3155:
3150:
3145:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3090:
3085:
3080:
3075:
3070:
3068:Bosch reaction
3065:
3060:
3055:
3050:
3045:
3040:
3035:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2995:
2990:
2985:
2979:
2977:
2973:Organic redox
2969:
2968:
2966:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2894:
2892:
2886:
2885:
2883:
2882:
2877:
2872:
2867:
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2827:
2822:
2817:
2812:
2807:
2805:Esterification
2802:
2797:
2792:
2787:
2782:
2776:
2774:
2766:
2765:
2762:
2761:
2759:
2758:
2753:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2652:
2650:
2646:
2645:
2643:
2642:
2637:
2632:
2627:
2622:
2617:
2612:
2606:
2604:
2595:
2594:
2589:
2584:
2582:Wurtz reaction
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2452:Prins reaction
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2349:
2344:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2267:Hydrocyanation
2264:
2259:
2254:
2249:
2244:
2239:
2237:Henry reaction
2234:
2229:
2224:
2219:
2214:
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2149:
2144:
2139:
2134:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1937:Aldol reaction
1934:
1929:
1924:
1918:
1916:
1911:Carbon-carbon
1908:
1907:
1896:
1895:
1890:
1888:Zaitsev's rule
1885:
1880:
1875:
1870:
1865:
1860:
1855:
1850:
1845:
1840:
1835:
1833:Steric effects
1830:
1825:
1820:
1815:
1810:
1805:
1800:
1795:
1790:
1785:
1780:
1775:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1670:
1665:
1660:
1655:
1650:
1645:
1640:
1635:
1630:
1625:
1620:
1615:
1610:
1605:
1600:
1595:
1590:
1585:
1580:
1575:
1570:
1565:
1560:
1555:
1550:
1545:
1540:
1535:
1530:
1525:
1520:
1514:
1511:
1510:
1508:
1507:
1502:
1497:
1492:
1487:
1485:Redox reaction
1482:
1477:
1472:
1470:Polymerization
1467:
1462:
1456:
1453:
1452:
1444:
1443:
1436:
1429:
1421:
1415:
1414:
1409:
1402:
1401:External links
1399:
1396:
1395:
1351:
1324:
1299:
1292:
1274:
1251:
1224:
1197:
1170:
1164:978-3527306732
1163:
1135:
1128:
1095:
1088:
1056:
1055:
1053:
1050:
1049:
1048:
1043:
1038:
1036:Naphthoquinone
1033:
1026:
1023:
1010:
1004:
1001:
996:
993:
984:
981:
925:
922:
919:Anthraquinones
914:
911:
898:
895:
887:
886:
875:
868:naphthoquinone
860:
857:anthraquinones
851:
834:
818:
815:
763:
754:
745:
724:, also called
717:
714:
713:
708:
686:
685:
681:standard state
678:
675:
674:
664:
661:
658:
657:
653:
652:
649:
643:
642:
617:
612:
609:
608:
603:
598:
595:
594:
589:
584:
581:
580:
573:
568:
565:
564:
554:
553:
550:
547:
544:
543:
534:
533:
529:
528:
525:
520:
517:
516:
513:
507:
506:
503:
497:
496:
489:
483:
482:
479:
475:
474:
468:
462:
461:
458:
452:
446:
441:
436:
433:
432:
428:
427:
425:
424:
421:
413:
412:
411:
408:
407:
405:
404:
400:
397:
396:
388:
387:
386:
383:
382:
380:
379:
366:
364:
352:
349:
348:
345:
339:
338:
336:
335:
327:
325:
319:
318:
316:
315:
311:
309:
303:
302:
300:
299:
291:
289:
281:
278:
277:
275:
274:
266:
264:
258:
257:
254:
249:
246:
245:
235:
227:
226:
224:
223:
215:
213:
207:
206:
204:
203:
195:
193:
187:
186:
184:
183:
175:
173:
167:
166:
163:
158:
155:
154:
152:
151:
143:
141:
134:
131:
130:
128:
127:
119:
117:
112:
109:
108:
104:
103:
100:
99:
96:
93:
90:
87:
84:
81:
78:
75:
71:
70:
66:
65:
61:
60:
54:
53:
49:
48:
40:
39:
31:
30:
15:
9:
6:
4:
3:
2:
4748:
4737:
4734:
4733:
4731:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4648:
4645:
4643:
4640:
4638:
4635:
4633:
4630:
4628:
4627:Herz reaction
4625:
4623:
4620:
4618:
4615:
4613:
4610:
4608:
4605:
4603:
4600:
4598:
4595:
4593:
4590:
4588:
4585:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4548:
4545:
4543:
4540:
4538:
4535:
4533:
4530:
4528:
4525:
4523:
4520:
4518:
4515:
4513:
4510:
4508:
4505:
4504:
4502:
4498:
4492:
4489:
4487:
4484:
4482:
4479:
4477:
4474:
4472:
4469:
4467:
4464:
4462:
4459:
4457:
4454:
4452:
4449:
4447:
4444:
4442:
4439:
4437:
4434:
4432:
4429:
4427:
4424:
4422:
4419:
4417:
4414:
4412:
4409:
4407:
4404:
4402:
4399:
4397:
4394:
4392:
4389:
4387:
4384:
4382:
4379:
4377:
4374:
4372:
4369:
4367:
4364:
4362:
4359:
4357:
4354:
4352:
4349:
4347:
4344:
4342:
4339:
4337:
4334:
4333:
4331:
4329:
4328:Cycloaddition
4325:
4319:
4316:
4314:
4311:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4289:
4286:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4266:
4264:
4261:
4259:
4256:
4254:
4251:
4249:
4246:
4244:
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4173:Isay reaction
4171:
4169:
4166:
4164:
4161:
4159:
4156:
4154:
4151:
4149:
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4068:Cycloaddition
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3970:
3968:
3966:
3963:Ring forming
3960:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3931:
3929:
3926:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3863:Rupe reaction
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3485:
3483:
3481:
3475:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3253:Ley oxidation
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3218:Hydroxylation
3216:
3214:
3211:
3209:
3208:Hydrogenation
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3151:
3149:
3146:
3144:
3143:DNA oxidation
3141:
3139:
3136:
3134:
3133:Deoxygenation
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3023:Aromatization
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2980:
2978:
2976:
2970:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2895:
2893:
2887:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2860:Reed reaction
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2777:
2775:
2771:bond forming
2767:
2757:
2754:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2676:Cope reaction
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2653:
2651:
2647:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2607:
2605:
2603:
2599:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2387:Nef synthesis
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2362:Methylenation
2360:
2358:
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2232:Heck reaction
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1919:
1917:
1913:bond forming
1909:
1905:
1900:
1894:
1891:
1889:
1886:
1884:
1881:
1879:
1878:Y-aromaticity
1876:
1874:
1871:
1869:
1866:
1864:
1863:Walsh diagram
1861:
1859:
1856:
1854:
1851:
1849:
1848:Taft equation
1846:
1844:
1841:
1839:
1836:
1834:
1831:
1829:
1826:
1824:
1821:
1819:
1818:ÎŁ-aromaticity
1816:
1814:
1811:
1809:
1806:
1804:
1801:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1743:Marcus theory
1741:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1718:HĂŒckel's rule
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1673:Evelyn effect
1671:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1653:Electron-rich
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1591:
1589:
1586:
1584:
1581:
1579:
1576:
1574:
1571:
1569:
1568:Bema Hapothle
1566:
1564:
1561:
1559:
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1515:
1512:
1506:
1503:
1501:
1498:
1496:
1493:
1491:
1488:
1486:
1483:
1481:
1478:
1476:
1473:
1471:
1468:
1466:
1463:
1461:
1458:
1457:
1454:
1450:
1442:
1437:
1435:
1430:
1428:
1423:
1422:
1419:
1413:
1410:
1408:
1405:
1404:
1391:
1387:
1382:
1377:
1373:
1369:
1362:
1355:
1340:. New Zealand
1339:
1335:
1328:
1314:on 2009-06-09
1313:
1309:
1303:
1295:
1293:0-89852-340-0
1289:
1285:
1278:
1270:
1266:
1262:
1255:
1247:
1243:
1239:
1235:
1228:
1220:
1216:
1212:
1208:
1201:
1193:
1189:
1185:
1181:
1174:
1166:
1160:
1156:
1152:
1148:
1147:
1139:
1131:
1125:
1121:
1117:
1113:
1109:
1105:
1099:
1091:
1089:9781498754293
1085:
1081:
1077:
1076:
1068:
1066:
1064:
1062:
1057:
1047:
1044:
1042:
1039:
1037:
1034:
1032:
1029:
1028:
1022:
1020:
1015:
1013:
1000:
995:Other isomers
992:
990:
980:
978:
974:
970:
966:
965:hemicellulose
962:
958:
954:
951:
947:
943:
939:
935:
931:
920:
910:
908:
904:
894:
892:
884:
880:
876:
873:
869:
865:
861:
858:
854:
847:
843:
839:
835:
832:
828:
824:
823:
822:
814:
812:
808:
804:
800:
796:
792:
788:
784:
780:
776:
772:
739:with formula
738:
735:
731:
727:
723:
722:Anthraquinone
711:
704:
699:
682:
676:
673:
668:
665:
660:
659:
654:
650:
648:
645:
644:
618:
615:
611:
610:
604:
601:
597:
596:
593:
590:
587:
583:
582:
578:
574:
571:
567:
566:
562:
560:
555:
551:
546:
545:
541:
540:
535:
530:
526:
523:
519:
518:
514:
512:
511:Boiling point
509:
508:
504:
502:
501:Melting point
499:
498:
490:
488:
485:
484:
481:Yellow solid
480:
477:
476:
469:
467:
464:
463:
442:
439:
435:
434:
429:
420:
419:
416:
409:
395:
394:
391:
384:
376:
372:
371:DTXSID3020095
368:
367:
365:
355:
351:
350:
346:
344:
341:
340:
333:
329:
328:
326:
324:
321:
320:
313:
312:
310:
308:
305:
304:
297:
293:
292:
290:
284:
280:
279:
272:
268:
267:
265:
263:
260:
259:
255:
252:
248:
247:
243:
239:
236:
234:
232:ECHA InfoCard
229:
228:
221:
217:
216:
214:
212:
209:
208:
201:
197:
196:
194:
192:
189:
188:
181:
177:
176:
174:
172:
169:
168:
164:
161:
157:
156:
149:
145:
144:
142:
138:
133:
132:
125:
121:
120:
118:
115:
111:
110:
105:
97:
94:
91:
88:
85:
82:
79:
76:
74:Anthraquinone
73:
72:
67:
59:
55:
50:
46:
41:
37:
32:
28:
23:
3668:Ene reaction
3028:Autoxidation
2889:Degradation
2780:Azo coupling
2557:Ugi reaction
2157:Ene reaction
1957:Alkynylation
1808:Polyfluorene
1803:Polar effect
1668:Electrophile
1583:Bredt's rule
1553:Baird's rule
1523:Alpha effect
1371:
1367:
1354:
1342:. Retrieved
1337:
1327:
1316:. Retrieved
1312:the original
1302:
1283:
1277:
1260:
1254:
1237:
1233:
1227:
1210:
1206:
1200:
1183:
1179:
1173:
1144:
1138:
1107:
1098:
1073:
1031:Benzoquinone
1016:
1006:
998:
986:
977:kappa number
927:
913:Applications
900:
888:
831:Chromium(VI)
820:
729:
725:
721:
720:
591:
558:
548:Main hazards
537:
307:RTECS number
107:Identifiers
69:Other names
2167:Ethenolysis
1813:Ring strain
1783:Nucleophile
1608:Clar's rule
1548:Aromaticity
1344:11 November
647:Flash point
586:Signal word
542:(OHS/OSH):
478:Appearance
431:Properties
238:100.001.408
200:ChEMBL55659
180:CHEBI:40448
80:Anthradione
4451:Ozonolysis
3978:Annulation
3328:Ozonolysis
1447:Topics in
1318:2009-09-22
1269:1853/24767
1052:References
983:Niche uses
930:paper pulp
917:See also:
827:anthracene
769:. Several
672:anthracene
570:Pictograms
527:Insoluble
466:Molar mass
332:030MS0JBDO
211:ChemSpider
135:3D model (
114:CAS Number
3965:reactions
3480:reactions
2975:reactions
2891:reactions
2773:reactions
1915:reactions
1080:CRC Press
961:cellulose
897:Reactions
872:butadiene
817:Synthesis
795:catalysts
783:wood pulp
632:P308+P313
561:labelling
343:UN number
314:CB4725000
4730:Category
1858:Vinylogy
1528:Annulene
1475:Reagents
1106:(2014).
1041:Parietin
1025:See also
953:catalyst
934:alkaline
907:anthrone
734:aromatic
732:, is an
532:Hazards
1518:A value
1390:1339448
946:Soda-AQ
944:or the
942:sulfite
879:styrene
842:benzene
811:hoelite
807:ethanol
799:soluble
771:isomers
703:what is
701: (
667:quinone
487:Density
471:208.216
283:PubChem
256:102870
165:390030
124:84-65-1
92:Hoelite
1388:
1290:
1240:: 15.
1213:: 72.
1161:
1126:
1086:
1019:UGT1A8
1003:Safety
973:lignin
698:verify
695:
592:Danger
493:
415:SMILES
271:C16207
191:ChEMBL
98:Corbit
95:Morkit
52:Names
1364:(PDF)
1186:: 4.
950:redox
938:kraft
803:water
775:IUPAC
495:g/cm
491:1.438
390:InChI
347:3143
171:ChEBI
137:JSmol
1386:PMID
1346:2014
1288:ISBN
1159:ISBN
1124:ISBN
1084:ISBN
963:and
883:BASF
870:and
862:The
850:AlCl
844:and
836:The
791:dyes
779:keto
640:P501
636:P405
628:P281
624:P202
620:P201
606:H350
323:UNII
296:6780
262:KEGG
220:6522
1376:doi
1372:267
1265:hdl
1242:doi
1215:doi
1188:doi
1151:doi
1116:doi
989:kea
932:by
866:of
840:of
801:in
728:or
559:GHS
359:EPA
286:CID
4732::
1384:.
1370:.
1366:.
1336:.
1238:18
1236:.
1211:18
1209:.
1184:14
1182:.
1157:.
1122:.
1110:.
1060:^
1011:50
1009:LD
979:.
893:.
829:.
813:.
746:14
638:,
634:,
630:,
626:,
622:,
563::
447:14
1440:e
1433:t
1426:v
1392:.
1378::
1348:.
1321:.
1296:.
1271:.
1267::
1248:.
1244::
1221:.
1217::
1194:.
1190::
1167:.
1153::
1132:.
1118::
1092:.
885:.
859:.
852:3
764:2
759:O
755:8
750:H
741:C
693:N
669:,
459:2
456:O
453:8
450:H
444:C
361:)
357:(
139:)
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