2186:
1534:
1321:
2409:
429:
278:
1452:
2217:
1510:
1337:
625:
1367:
48:
68:
844:
620:
615:
78:
840:
38:
1352:
1235:
1035:
2270:
2301:
845:
1437:, and furan are, respectively, 152, 88, 121, and 67 kJ/mol (36, 21, 29, and 16 kcal/mol). Thus, these heterocycles, especially furan, are far less aromatic than benzene, as is manifested in the lability of these rings. The molecule is flat but the C=C groups attached to oxygen retain significant
843:
861:
633:
595:
2422:
Waizenegger, J.; Winkler, G.; Kuballa, T.; Ruge, W.; Kersting, M.; Alexy, U.; Lachenmeier, D. W. (2012). "Analysis and risk assessment of furan in coffee products targeted to adolescents".
2046:
James A. Marshall, Clark A. Sehon (1999). "Isomerization of b-Alkynyl
Allylic Alcohols to Furans Catalyzed by Silver Nitrate on Silica Gel: 2-Pentyl-3-Methyl-5-Heptylfuran".
2005:
Adam Sniady, Marco S. Morreale, Roman
Dembinski (2007). "Electrophilic Cyclization with N-Iodosuccinimide: Preparation of 5-(4-Bromophenyl)-3-Iodo-2-(4-Methyl-Phenyl)Furan".
846:
767:
1519:
3007:
1048:
1444:
Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.
2236:
1815:
1465:
Because of its partial aromatic character, furan's behavior is intermediate between that of an enol ether and an aromatic ring. It is dissimilar vs
2032:
1958:
Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. (1998). "Regioselective syntheses of substituted furans".
2567:
478:
1509:
948:
1320:
868:
775:
1351:
1336:
2134:
1551:
reactions, due to the electron-donating effects of the oxygen heteroatom. It reacts with bromine at 0 °C to give 2-bromofuran.
2130:"The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid"
2112:
2088:
1749:
1366:
703:
1797:
1533:
47:
2560:
2997:
2253:
1832:
1451:
1857:
1782:
443:
1649:
Exposure to furan at doses about 2,000 times the projected level of human exposure from foods increases the risk of
854:
1055:
1523:
1043:
2489:
3002:
2553:
2379:
2540:
1441:
character. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system.
1639:
1476:
Like enol ethers, 2,5-disubstituted furans are susceptible to hydrolysis to reversibly give 1,4-diketones.
759:
109:
1813:
Hoydonckx, H. E.; Van Rhijn, W. M.; Van Rhijn, W.; De Vos, D. E.; Jacobs, P. A. "Furfural and
Derivatives".
1182:
771:
689:
376:
273:
2271:"Industrially Applicable Strategies for Mitigating Acrylamide, Furan and 5-Hydroxymethylfurfural in Food"
2078:
407:
235:
37:
751:
624:
1733:
1548:
1274:
699:
619:
67:
1695:
285:
2408:
1643:
1730:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1484:
1302:
891:
424:
77:
2465:
578:
614:
1103:
677:
20:
2026:
1960:
1250:
1071:
715:
647:
607:
2323:"Furan in heat-treated foods: Formation, exposure, toxicity, and aspects of risk assessment"
1774:
1767:
2787:
2576:
2187:"Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties"
2182:
1700:
1571:
1402:
1290:
1174:
1143:
799:
385:
97:
783:
255:
183:
8:
2905:
1620:
779:
159:
149:
2384:"Update on furan levels in food from monitoring years 2004–2010 and exposure assessment"
1495:)-3-nitroacrylate. The reaction product is a mixture of isomers with preference for the
1410:
428:
277:
215:
2520:
2447:
2361:
2321:
Moro, S.; Chipman, J. K.; Wegener, J. W.; Hamberger, C.; Dekant, W.; Mally, A. (2012).
2158:
2129:
1873:
1654:
1190:
1010:
723:
195:
1973:
2865:
2512:
2439:
2353:
2293:
2249:
2209:
2163:
2108:
2084:
1936:
1853:
1828:
1778:
1745:
1705:
989:
942:
2524:
2451:
2365:
2322:
1193:
in 1870, although he called it "tetraphenol" (as if it were a four-carbon analog to
2824:
2504:
2431:
2395:
2345:
2337:
2285:
2241:
2201:
2153:
2143:
2055:
2014:
1969:
1897:
1820:
1737:
1635:
1426:
1081:
1074:
501:
1824:
2992:
2819:
2435:
1710:
1685:
1564:
1470:
1246:
984:
904:
739:
349:
304:
1931:
1741:
1518:
Diels-Alder reaction of furan with arynes provides corresponding derivatives of
1277:
is a classic way to synthesize furans. The reaction involves alkylation of 1,3-
1095:
atom. Chemical compounds containing such rings are also referred to as furans.
711:
2870:
2860:
2814:
2602:
2004:
1680:
1376:
1186:
1026:
811:
731:
681:
2508:
930:
787:
727:
2986:
2900:
2895:
2875:
2845:
2470:
2400:
2383:
2245:
2059:
2018:
1901:
1556:
1466:
1226:
1170:
1119:
1107:
743:
567:
557:
266:
755:
19:
This article is about the industrial chemical compound. For other uses, see
2931:
2516:
2443:
2357:
2341:
2297:
2213:
2167:
1650:
1575:
1560:
1372:
1282:
1139:
997:
2148:
867:
807:
2951:
2941:
2936:
2921:
2890:
2663:
2181:
Filatov, M. A.; Baluschev, S.; Ilieva, I. Z.; Enkelmann, V.; Miteva, T.;
2074:
1674:
1496:
1438:
962:
880:
791:
2545:
1619:
Furan is found in heat-treated commercial foods and is produced through
853:
763:
2840:
2714:
2709:
2466:"Espresso makers: Coffee in capsules contains more furan than the rest"
1658:
1488:
1327:
1234:
1169:
is produced from bran). The first furan derivative to be described was
1131:
993:
860:
526:
286:
246:
2349:
2289:
2205:
1281:
with α-bromoketones followed by dehydration of an intermediate hydroxy
2946:
2926:
2855:
2729:
2724:
2678:
2673:
2653:
2638:
2633:
2628:
2128:
Masesane, I.; Batsanov, A.; Howard, J.; Modal, R.; Steel, P. (2006).
1628:
1434:
1418:
1394:
1342:
1258:
1214:
1099:
972:
695:
396:
1877:
1025:
Except where otherwise noted, data are given for materials in their
2885:
2734:
2719:
2704:
2699:
2668:
2658:
2643:
2597:
1690:
1632:
1589:
1398:
1390:
1357:
1278:
1242:
1218:
1178:
1166:
1078:
826:
653:
324:
819:
669:
182:
2967:
2771:
2755:
2750:
2694:
2648:
2623:
2045:
1670:
1600:
1585:
1581:
1544:
1430:
1422:
1414:
1254:
1123:
1115:
1111:
968:
735:
547:
336:
2080:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
2880:
2850:
2269:
Anese, M.; Manzocco, L.; Calligaris, S.; Nicoli, M. C. (2013).
2180:
2107:(5th ed.). Upper Saddle River, NJ: Pearson Prentice Hall.
1624:
1593:
1286:
1222:
1194:
1092:
1085:
747:
226:
2378:
1917:
Chemistry of Carbon
Compounds: A Modern Comprehensive Treatise
2421:
2268:
2072:
1812:
1480:
1155:
1135:
1127:
803:
360:
206:
172:
707:
412:
2320:
2127:
1646:, although the levels are still within safe health limits.
1308:
Many routes exist for the synthesis of substituted furans.
1262:
1162:
1110:
close to room temperature. It is soluble in common organic
1088:
315:
2083:(6th ed.), New York: Wiley-Interscience, p. 62,
719:
1623:
of natural food constituents. It can be found in roasted
1657:
in rats. Furan is therefore listed as a possible human
1522:, which are useful intermediates in synthesis of other
1142:
in humans. Furan is used as a starting point for other
1677:
as thermoset FRP for chemical process plant equipments
1285:. The other traditional route involve the reaction of
2490:"Toxicity and carcinogenicity of furan in human diet"
1994:(3rd ed.). Liverpool: Longman. p. 209-212.
1584:
can be prepared industrially by treating furan with
1360:, derived from sugars, is the major source of furans
661:
1413:). The aromaticity is modest relative to that for
1766:
657:
1642:contain more furan than that made in traditional
2984:
2185:; Aleshchenkov, S. E.; Cheprakov, A. V. (2012).
1957:
1764:
665:
348:
842:
158:
2237:Ullmann's Encyclopedia of Industrial Chemistry
1890:Berichte der Deutschen Chemischen Gesellschaft
1816:Ullmann's Encyclopedia of Industrial Chemistry
1765:Jakubke, Hans Dieter; Jeschkeit, Hans (1994).
1241:In the laboratory, furan can be obtained from
1185:in 1831 and characterised nine years later by
815:
673:
2561:
1631:. Research has indicated that coffee made in
562:−85.6 °C (−122.1 °F; 187.6 K)
51:Skeletal formula showing numbering convention
2487:
2031:: CS1 maint: multiple names: authors list (
1245:by oxidation to 2-furoic acid, followed by
1213:Industrially, furan is manufactured by the
2568:
2554:
2483:
2481:
2278:Journal of Agricultural and Food Chemistry
795:
572:31.3 °C (88.3 °F; 304.4 K)
427:
276:
254:
3008:Substances discovered in the 19th century
2575:
2424:Food Additives & Contaminants: Part A
2399:
2157:
2147:
1989:
1872:
1808:
1806:
384:
1722:
1384:
2478:
2330:Molecular Nutrition & Food Research
2316:
2314:
2227:
1850:Elsevier's Dictionary of Chemoetymology
1847:
1177:in 1780. Another important derivative,
423:
2985:
2135:Beilstein Journal of Organic Chemistry
2102:
1985:
1983:
1929:
1803:
1543:It is considerably more reactive than
1345:, an aroma compound found in rose oil.
1268:
1249:. It can also be prepared directly by
899:390 °C (734 °F; 663 K)
885:−36 °C (−33 °F; 237 K)
267:
2549:
2234:Harreus, Albrecht Ludwig. "Pyrrole".
1798:DHHS (NIOSH) Publication No. 2016–171
1189:. Furan itself was first prepared by
455:Key: YLQBMQCUIZJEEH-UHFFFAOYSA-N
234:
214:
2311:
1914:
1409: + 2 aromatic system (see
2233:
1980:
465:Key: YLQBMQCUIZJEEH-UHFFFAOYAC
339:
323:
13:
2488:Bakhiya, N.; Appel, K. E. (2010).
1130:. Its odor is "strong, ethereal;
838:
76:
66:
46:
36:
14:
3019:
2534:
1769:Concise Encyclopedia of Chemistry
452:InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
2407:
1627:, instant coffee, and processed
1532:
1508:
1450:
1365:
1350:
1335:
1319:
1233:
1154:The name "furan" comes from the
1077:, consisting of a five-membered
1033:
623:
618:
613:
513:
462:InChI=1/C4H4O/c1-2-4-5-3-1/h1-4H
41:Full structural formula of furan
2458:
2415:
2372:
2262:
2174:
2121:
2096:
2066:
2039:
1998:
1559:of furans sequentially affords
1326:The drug Zantac, also known as
1029:(at 25 °C , 100 kPa).
2380:European Food Safety Authority
1951:
1923:
1908:
1866:
1841:
1791:
1773:. Walter de Gruyter. pp.
1758:
1734:The Royal Society of Chemistry
1588:in the presence of solid acid
1217:-catalyzed decarbonylation of
519:
507:
16:Heterocyclic organic compound,
1:
1990:Gilchrist, Thomas L. (1997).
1974:10.1016/S0040-4020(97)10303-9
1825:10.1002/14356007.a12_119.pub2
1716:
1524:polycyclic aromatic compounds
1460:
1393:character because one of the
1208:
1126:, and is slightly soluble in
2436:10.1080/19440049.2011.617012
1315:Furan in nature and commerce
7:
1915:Rodd, Ernest Harry (1971).
1848:Senning, Alexander (2006).
1742:10.1039/9781849733069-FP001
1664:
1405:into the ring, creating a 4
1257:-containing materials, and
919:or concentration (LD, LC):
911:Upper: 14.3% at 20 °C
542:Colorless, volatile liquid
62:
32:
10:
3024:
1946:, vol. 1, p. 274
1574:, furans are converted to
1549:electrophilic substitution
1183:Johann Wolfgang Döbereiner
1149:
18:
2998:IARC Group 2B carcinogens
2960:
2914:
2833:
2807:
2800:
2780:
2764:
2743:
2687:
2611:
2590:
2583:
2509:10.1007/s00204-010-0531-y
2103:Bruice, Paula Y. (2007).
1800:, p. 2, Accessed Nov 2019
1696:Furantetracarboxylic acid
1614:
1417:and related heterocycles
1023:
1003:
954:
915:
594:
589:
494:
474:
439:
142:
133:5-Oxacyclo-1,3-pentadiene
131:5-Oxacyclopenta-1,3-diene
122:
116:1-Oxacyclopenta-2,4-diene
108:
96:
91:
61:
31:
2541:Recent synthetic methods
2401:10.2903/j.efsa.2011.2347
2246:10.1002/14356007.a22_453
2060:10.15227/orgsyn.076.0263
2019:10.15227/orgsyn.084.0199
1902:10.1002/cber.18700030129
1878:"Ueber das Tetraphenol C
1487:with electron-deficient
1225:-catalyzed oxidation of
690:Precautionary statements
2240:. Weinheim: Wiley-VCH.
1819:. Weinheim: Wiley-VCH.
579:Magnetic susceptibility
129:1,4-Epoxy-1,3-butadiene
114:1,4-Epoxybuta-1,3-diene
2497:Archives of Toxicology
2342:10.1002/mnfr.201200093
1992:Heterocyclic Chemistry
1930:Wilson, W. C. (1941).
1401:on the oxygen atom is
1275:Feist–Benary synthesis
1098:Furan is a colorless,
849:
82:
72:
52:
42:
21:Furan (disambiguation)
3003:Simple aromatic rings
2577:Simple aromatic rings
2149:10.1186/1860-5397-2-9
1736:. 2014. p. 392.
1701:Simple aromatic rings
1653:in rats and mice and
1651:hepatocellular tumors
1638:and coffee made from
1485:Diels–Alder reactions
1385:Structure and bonding
1251:thermal decomposition
848:
110:Systematic IUPAC name
80:
70:
50:
40:
2788:Cyclooctadecanonaene
1572:Achmatowicz reaction
1303:Paal–Knorr synthesis
1291:phosphorus pentoxide
1175:Carl Wilhelm Scheele
1144:speciality chemicals
831:(fire diamond)
98:Preferred IUPAC name
71:Ball-and-stick model
2906:5-Aza-7-deazapurine
2200:(24): 11119–11131.
2073:Smith, Michael B.;
1621:thermal degradation
1520:dihydronaphthalenes
1269:Synthesis of furans
1261:solids, especially
534: g·mol
196:Beilstein Reference
81:Space-filling model
28:
1644:drip coffee makers
1479:Furan serves as a
1427:resonance energies
1191:Heinrich Limpricht
1181:, was reported by
1056:Infobox references
955:Related compounds
937:> 2 g/kg (rat)
850:
83:
73:
53:
43:
26:
2980:
2979:
2976:
2975:
2866:Benzo(c)thiophene
2796:
2795:
2474:. April 14, 2011.
2290:10.1021/jf305085r
2206:10.1021/jo302135q
2114:978-0-13-196316-0
2105:Organic Chemistry
2090:978-0-471-72091-1
2048:Organic Syntheses
2007:Organic Syntheses
1968:(10): 1955–2020.
1944:Collected Volumes
1937:Organic Syntheses
1751:978-0-85404-182-4
1706:Furan fatty acids
1375:is a cofactor in
1064:Chemical compound
1062:
1061:
990:2,5-Dimethylfuran
980:Related compounds
943:Safety data sheet
648:Hazard statements
585:-43.09·10 cm/mol
408:CompTox Dashboard
184:Interactive image
87:
86:
57:
56:
3015:
2825:Trithiapentalene
2805:
2804:
2588:
2587:
2570:
2563:
2556:
2547:
2546:
2529:
2528:
2494:
2485:
2476:
2475:
2462:
2456:
2455:
2419:
2413:
2412:
2411:
2405:
2403:
2376:
2370:
2369:
2336:(8): 1197–1211.
2327:
2318:
2309:
2308:
2306:
2300:. Archived from
2284:(43): 10209–14.
2275:
2266:
2260:
2259:
2231:
2225:
2224:
2222:
2216:. Archived from
2191:
2178:
2172:
2171:
2161:
2151:
2125:
2119:
2118:
2100:
2094:
2093:
2070:
2064:
2063:
2043:
2037:
2036:
2030:
2022:
2002:
1996:
1995:
1987:
1978:
1977:
1955:
1949:
1947:
1940:
1927:
1921:
1920:
1912:
1906:
1905:
1870:
1864:
1863:
1845:
1839:
1838:
1810:
1801:
1795:
1789:
1788:
1772:
1762:
1756:
1755:
1726:
1655:bile duct tumors
1565:tetrahydrofurans
1536:
1512:
1454:
1369:
1354:
1339:
1323:
1237:
1075:organic compound
1046:
1040:
1037:
1036:
905:Explosive limits
870:
863:
856:
841:
821:
817:
813:
809:
805:
801:
797:
793:
789:
785:
781:
777:
773:
769:
765:
761:
757:
753:
749:
745:
741:
737:
733:
729:
725:
721:
717:
713:
709:
705:
701:
697:
683:
679:
675:
671:
667:
663:
659:
655:
627:
622:
617:
533:
521:
515:
509:
502:Chemical formula
432:
431:
416:
414:
388:
352:
341:
327:
305:Gmelin Reference
288:
280:
269:
258:
238:
218:
186:
162:
137:Divinylene oxide
63:
33:
29:
25:
3023:
3022:
3018:
3017:
3016:
3014:
3013:
3012:
2983:
2982:
2981:
2972:
2956:
2910:
2829:
2820:Thienothiophene
2792:
2776:
2760:
2739:
2683:
2607:
2579:
2574:
2537:
2532:
2492:
2486:
2479:
2464:
2463:
2459:
2420:
2416:
2406:
2377:
2373:
2325:
2319:
2312:
2304:
2273:
2267:
2263:
2256:
2232:
2228:
2220:
2189:
2179:
2175:
2126:
2122:
2115:
2101:
2097:
2091:
2071:
2067:
2044:
2040:
2024:
2023:
2003:
1999:
1988:
1981:
1956:
1952:
1942:
1928:
1924:
1913:
1909:
1885:
1881:
1871:
1867:
1860:
1846:
1842:
1835:
1811:
1804:
1796:
1792:
1785:
1763:
1759:
1752:
1728:
1727:
1723:
1719:
1711:Tetrahydrofuran
1686:Furanoflavonoid
1667:
1617:
1608:
1604:
1597:
1491:such as ethyl (
1471:tetrahydrofuran
1463:
1387:
1380:
1370:
1361:
1355:
1346:
1340:
1331:
1324:
1311:
1300:
1296:
1271:
1247:decarboxylation
1211:
1204:
1200:
1152:
1134:-like". It is
1065:
1058:
1053:
1052:
1051: ?)
1042:
1038:
1034:
1030:
1019:
1013:
996:
992:
988:
985:Tetrahydrofuran
981:
971:
965:
934:
928:
910:
896:
893:
875:
874:
873:
872:
865:
858:
851:
847:
839:
692:
650:
636:
610:
582:
531:
518:
512:
504:
490:
487:
482:
481:
470:
467:
466:
463:
457:
456:
453:
447:
446:
435:
417:
410:
391:
371:
355:
342:
330:
307:
298:
261:
241:
221:
198:
189:
176:
165:
152:
138:
136:
134:
132:
130:
128:
126:
118:
117:
115:
104:
103:
24:
17:
12:
11:
5:
3021:
3011:
3010:
3005:
3000:
2995:
2978:
2977:
2974:
2973:
2971:
2970:
2964:
2962:
2958:
2957:
2955:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2918:
2916:
2912:
2911:
2909:
2908:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2871:Benzophosphole
2868:
2863:
2861:Benzothiophene
2858:
2853:
2848:
2843:
2837:
2835:
2831:
2830:
2828:
2827:
2822:
2817:
2815:Diazapentalene
2811:
2809:
2802:
2798:
2797:
2794:
2793:
2791:
2790:
2784:
2782:
2778:
2777:
2775:
2774:
2768:
2766:
2762:
2761:
2759:
2758:
2753:
2747:
2745:
2744:Seven-membered
2741:
2740:
2738:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2691:
2689:
2685:
2684:
2682:
2681:
2676:
2671:
2666:
2661:
2656:
2651:
2646:
2641:
2636:
2631:
2626:
2621:
2615:
2613:
2609:
2608:
2606:
2605:
2603:Cyclopropenone
2600:
2594:
2592:
2591:Three-membered
2585:
2581:
2580:
2573:
2572:
2565:
2558:
2550:
2544:
2543:
2536:
2535:External links
2533:
2531:
2530:
2503:(7): 563–578.
2477:
2457:
2414:
2371:
2310:
2307:on 2017-08-08.
2261:
2255:978-3527306732
2254:
2226:
2223:on 2020-02-19.
2183:Landfester, K.
2173:
2120:
2113:
2095:
2089:
2065:
2038:
1997:
1979:
1950:
1922:
1907:
1883:
1879:
1865:
1858:
1840:
1834:978-3527306732
1833:
1802:
1790:
1783:
1757:
1750:
1720:
1718:
1715:
1714:
1713:
1708:
1703:
1698:
1693:
1688:
1683:
1681:Furanocoumarin
1678:
1666:
1663:
1616:
1613:
1612:
1611:
1606:
1602:
1595:
1579:
1568:
1553:
1552:
1540:
1539:
1538:
1537:
1516:
1515:
1514:
1513:
1462:
1459:
1458:
1457:
1456:
1455:
1386:
1383:
1382:
1381:
1377:methanogenesis
1371:
1364:
1362:
1356:
1349:
1347:
1341:
1334:
1332:
1325:
1318:
1316:
1298:
1294:
1270:
1267:
1239:
1238:
1210:
1207:
1202:
1198:
1187:John Stenhouse
1161:, which means
1151:
1148:
1106:liquid with a
1063:
1060:
1059:
1054:
1032:
1031:
1027:standard state
1024:
1021:
1020:
1017:
1014:
1009:
1006:
1005:
1001:
1000:
982:
979:
976:
975:
966:
960:
957:
956:
952:
951:
946:
939:
938:
935:
926:
924:
921:
920:
913:
912:
907:
901:
900:
897:
890:
887:
886:
883:
877:
876:
866:
859:
852:
837:
836:
835:
834:
832:
823:
822:
768:P303+P361+P353
693:
688:
685:
684:
651:
646:
643:
642:
637:
632:
629:
628:
611:
606:
603:
602:
592:
591:
587:
586:
583:
577:
574:
573:
570:
564:
563:
560:
554:
553:
550:
544:
543:
540:
536:
535:
529:
523:
522:
516:
510:
505:
500:
497:
496:
492:
491:
489:
488:
485:
477:
476:
475:
472:
471:
469:
468:
464:
461:
460:
458:
454:
451:
450:
442:
441:
440:
437:
436:
434:
433:
420:
418:
406:
403:
402:
399:
393:
392:
390:
389:
381:
379:
373:
372:
370:
369:
365:
363:
357:
356:
354:
353:
345:
343:
335:
332:
331:
329:
328:
320:
318:
312:
311:
308:
303:
300:
299:
297:
296:
292:
290:
282:
281:
271:
263:
262:
260:
259:
251:
249:
243:
242:
240:
239:
231:
229:
223:
222:
220:
219:
211:
209:
203:
202:
199:
194:
191:
190:
188:
187:
179:
177:
170:
167:
166:
164:
163:
155:
153:
148:
145:
144:
140:
139:
124:
120:
119:
113:
112:
106:
105:
101:
100:
94:
93:
89:
88:
85:
84:
74:
59:
58:
55:
54:
44:
15:
9:
6:
4:
3:
2:
3020:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2990:
2988:
2969:
2966:
2965:
2963:
2959:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2919:
2917:
2913:
2907:
2904:
2902:
2901:Benzothiazole
2899:
2897:
2896:Benzisoxazole
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2876:Benzimidazole
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2846:Isobenzofuran
2844:
2842:
2839:
2838:
2836:
2832:
2826:
2823:
2821:
2818:
2816:
2813:
2812:
2810:
2806:
2803:
2799:
2789:
2786:
2785:
2783:
2779:
2773:
2770:
2769:
2767:
2765:Nine-membered
2763:
2757:
2754:
2752:
2749:
2748:
2746:
2742:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2692:
2690:
2686:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2616:
2614:
2612:Five-membered
2610:
2604:
2601:
2599:
2596:
2595:
2593:
2589:
2586:
2582:
2578:
2571:
2566:
2564:
2559:
2557:
2552:
2551:
2548:
2542:
2539:
2538:
2526:
2522:
2518:
2514:
2510:
2506:
2502:
2498:
2491:
2484:
2482:
2473:
2472:
2471:Science Daily
2467:
2461:
2453:
2449:
2445:
2441:
2437:
2433:
2429:
2425:
2418:
2410:
2402:
2397:
2393:
2389:
2385:
2381:
2375:
2367:
2363:
2359:
2355:
2351:
2347:
2343:
2339:
2335:
2331:
2324:
2317:
2315:
2303:
2299:
2295:
2291:
2287:
2283:
2279:
2272:
2265:
2257:
2251:
2247:
2243:
2239:
2238:
2230:
2219:
2215:
2211:
2207:
2203:
2199:
2195:
2188:
2184:
2177:
2169:
2165:
2160:
2155:
2150:
2145:
2141:
2137:
2136:
2131:
2124:
2116:
2110:
2106:
2099:
2092:
2086:
2082:
2081:
2076:
2069:
2061:
2057:
2053:
2049:
2042:
2034:
2028:
2020:
2016:
2012:
2008:
2001:
1993:
1986:
1984:
1975:
1971:
1967:
1963:
1962:
1954:
1945:
1939:
1938:
1933:
1926:
1918:
1911:
1903:
1899:
1895:
1891:
1887:
1875:
1874:Limpricht, H.
1869:
1861:
1859:0-444-52239-5
1855:
1851:
1844:
1836:
1830:
1826:
1822:
1818:
1817:
1809:
1807:
1799:
1794:
1786:
1784:0-89925-457-8
1780:
1776:
1771:
1770:
1761:
1753:
1747:
1743:
1739:
1735:
1732:. Cambridge:
1731:
1725:
1721:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1676:
1672:
1669:
1668:
1662:
1660:
1656:
1652:
1647:
1645:
1641:
1637:
1634:
1630:
1626:
1622:
1609:
1598:
1591:
1587:
1583:
1580:
1577:
1573:
1569:
1566:
1562:
1561:dihydrofurans
1558:
1557:Hydrogenation
1555:
1554:
1550:
1546:
1542:
1541:
1535:
1531:
1530:
1529:
1528:
1527:
1525:
1521:
1511:
1507:
1506:
1505:
1504:
1503:
1501:
1499:
1494:
1490:
1486:
1482:
1477:
1474:
1472:
1468:
1453:
1449:
1448:
1447:
1446:
1445:
1442:
1440:
1436:
1432:
1428:
1424:
1420:
1416:
1412:
1411:Hückel's rule
1408:
1404:
1400:
1396:
1392:
1378:
1374:
1368:
1363:
1359:
1353:
1348:
1344:
1338:
1333:
1329:
1322:
1317:
1314:
1313:
1312:
1309:
1306:
1304:
1292:
1288:
1287:1,4-diketones
1284:
1280:
1276:
1266:
1264:
1260:
1256:
1252:
1248:
1244:
1236:
1232:
1231:
1230:
1228:
1227:1,3-butadiene
1224:
1220:
1216:
1206:
1196:
1192:
1188:
1184:
1180:
1176:
1172:
1171:2-furoic acid
1168:
1164:
1160:
1157:
1147:
1145:
1141:
1137:
1133:
1129:
1125:
1121:
1117:
1113:
1109:
1108:boiling point
1105:
1101:
1096:
1094:
1090:
1087:
1083:
1080:
1076:
1073:
1069:
1057:
1050:
1045:
1028:
1022:
1015:
1012:
1008:
1007:
1002:
999:
995:
991:
986:
983:
978:
977:
974:
970:
967:
964:
959:
958:
953:
950:
947:
944:
941:
940:
936:
932:
923:
922:
918:
914:
908:
906:
903:
902:
898:
895:
889:
888:
884:
882:
879:
878:
871:
864:
857:
833:
830:
829:
825:
824:
694:
691:
687:
686:
652:
649:
645:
644:
641:
638:
635:
631:
630:
626:
621:
616:
612:
609:
605:
604:
600:
598:
593:
588:
584:
580:
576:
575:
571:
569:
568:Boiling point
566:
565:
561:
559:
558:Melting point
556:
555:
551:
549:
546:
545:
541:
538:
537:
530:
528:
525:
524:
506:
503:
499:
498:
493:
484:
483:
480:
473:
459:
449:
448:
445:
438:
430:
426:
425:DTXSID6020646
422:
421:
419:
409:
405:
404:
400:
398:
395:
394:
387:
383:
382:
380:
378:
375:
374:
367:
366:
364:
362:
359:
358:
351:
347:
346:
344:
338:
334:
333:
326:
322:
321:
319:
317:
314:
313:
309:
306:
302:
301:
294:
293:
291:
289:
284:
283:
279:
275:
272:
270:
268:ECHA InfoCard
265:
264:
257:
253:
252:
250:
248:
245:
244:
237:
233:
232:
230:
228:
225:
224:
217:
213:
212:
210:
208:
205:
204:
200:
197:
193:
192:
185:
181:
180:
178:
174:
169:
168:
161:
157:
156:
154:
151:
147:
146:
141:
121:
111:
107:
99:
95:
90:
79:
75:
69:
65:
64:
60:
49:
45:
39:
35:
34:
30:
22:
2961:Five + Seven
2932:Isoquinoline
2688:Six-membered
2618:
2500:
2496:
2469:
2460:
2430:(1): 19–28.
2427:
2423:
2417:
2391:
2388:EFSA Journal
2387:
2374:
2333:
2329:
2302:the original
2281:
2277:
2264:
2235:
2229:
2218:the original
2197:
2194:J. Org. Chem
2193:
2176:
2139:
2133:
2123:
2104:
2098:
2079:
2075:March, Jerry
2068:
2051:
2047:
2041:
2027:cite journal
2010:
2006:
2000:
1991:
1965:
1959:
1953:
1943:
1935:
1925:
1916:
1910:
1896:(1): 90–91.
1893:
1889:
1868:
1852:. Elsevier.
1849:
1843:
1814:
1793:
1768:
1760:
1729:
1724:
1648:
1618:
1576:dihydropyran
1517:
1497:
1492:
1478:
1475:
1464:
1443:
1429:of benzene,
1406:
1388:
1373:methanofuran
1310:
1307:
1283:dihydrofuran
1272:
1240:
1221:, or by the
1212:
1158:
1153:
1140:carcinogenic
1114:, including
1097:
1072:heterocyclic
1067:
1066:
998:Dibenzofuran
963:heterocycles
916:
892:Autoignition
827:
639:
596:
361:RTECS number
236:ChEMBL278980
143:Identifiers
123:Other names
2952:Phthalazine
2942:Quinazoline
2937:Quinoxaline
2922:Naphthalene
2891:Benzoxazole
2808:Five + Five
2781:18-membered
2664:Isothiazole
2394:(9): 2347.
1961:Tetrahedron
1919:. Elsevier.
1675:Furan resin
1489:dienophiles
1439:double bond
1403:delocalized
1138:and may be
1011:Point group
931:median dose
917:Lethal dose
909:Lower: 2.3%
894:temperature
881:Flash point
634:Signal word
552:0.936 g/mL
539:Appearance
495:Properties
274:100.003.390
216:CHEBI:35559
127:Oxaannulene
2987:Categories
2841:Benzofuran
2834:Five + Six
2715:Pyridazine
2710:Pyrimidine
2350:1871/41889
1717:References
1659:carcinogen
1629:baby foods
1592:, such as
1578:compounds.
1461:Reactivity
1395:lone pairs
1389:Furan has
1328:ranitidine
1259:cellulosic
1209:Production
1132:chloroform
1084:with four
1004:Structure
994:Benzofuran
608:Pictograms
527:Molar mass
386:UC0XV6A8N9
247:ChemSpider
171:3D model (
150:CAS Number
2947:Cinnoline
2927:Quinoline
2915:Six + Six
2856:Isoindole
2730:Pentazine
2725:Tetrazine
2679:Pentazole
2674:Tetrazole
2654:Isoxazole
2639:Phosphole
2634:Thiophene
2629:Imidazole
1590:catalysts
1435:thiophene
1419:thiophene
1399:electrons
1343:Rosefuran
1301:) in the
1279:diketones
1215:palladium
1102:, highly
1100:flammable
973:Thiophene
812:P403+P235
808:P370+P378
800:P332+P313
780:P308+P313
776:P304+P340
772:P304+P312
764:P302+P352
760:P301+P312
599:labelling
397:UN number
368:LT8524000
295:203-727-3
287:EC Number
2886:Indazole
2735:Hexazine
2720:Triazine
2705:Pyrazine
2700:Pyridine
2669:Triazole
2659:Thiazole
2644:Pyrazole
2598:Borirene
2525:19389984
2517:20237914
2452:29027966
2444:22035212
2382:(2011).
2366:12446132
2358:22641279
2298:23627283
2214:23205621
2168:16674802
2142:(9): 9.
2077:(2007),
1876:(1870).
1691:Furanose
1665:See also
1640:capsules
1633:espresso
1469:such as
1391:aromatic
1358:Furfural
1243:furfural
1219:furfural
1179:furfural
1167:furfural
1112:solvents
1104:volatile
1091:and one
1079:aromatic
961:Related
949:Pennakem
828:NFPA 704
590:Hazards
581:(χ)
160:110-00-9
135:Furfuran
2968:Azulene
2801:2 rings
2772:Azonine
2756:Tropone
2751:Borepin
2695:Benzene
2649:Oxazole
2624:Pyrrole
2159:1524792
2054:: 263.
2013:: 199.
1932:"Furan"
1671:BS 4994
1586:ammonia
1582:Pyrrole
1570:In the
1545:benzene
1431:pyrrole
1423:pyrrole
1415:benzene
1255:pentose
1150:History
1124:acetone
1116:alcohol
1049:what is
1047: (
969:Pyrrole
548:Density
486:c1ccoc1
337:PubChem
201:103221
2993:Furans
2881:Purine
2851:Indole
2584:1 ring
2523:
2515:
2450:
2442:
2364:
2356:
2296:
2252:
2212:
2166:
2156:
2111:
2087:
1856:
1831:
1781:
1775:1–1201
1748:
1636:makers
1625:coffee
1615:Safety
1500:isomer
1467:ethers
1425:. The
1265:wood.
1223:copper
1195:phenol
1159:furfur
1122:, and
1093:oxygen
1086:carbon
1044:verify
1041:
945:(SDS)
640:Danger
532:68.075
479:SMILES
325:C14275
310:25716
227:ChEMBL
92:Names
27:Furan
2619:Furan
2521:S2CID
2493:(PDF)
2448:S2CID
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