772:
698:
611:
594:
298:
827:
The aryl halides produced on the largest scale are chlorobenzene and the isomers of dichlorobenzene. One major but discontinued application was the use of chlorobenzene as a solvent for dispersing the herbicide Lasso. Overall, production of aryl chlorides (also naphthyl derivatives) has been
281:
derivatives. Arenes with electron donating groups react with halogens even in the absence of Lewis acids. For example, phenols and anilines react quickly with chlorine and bromine water to give multihalogenated products. Many detailed laboratory procedures are available. For alkylbenzene
536:
were used extensively from the 1930s to 1950s in cable and capacitor production, due to their insulating, hydrophobic, and flame retardant properties, but they have since been phased out for this use due to toxicity, environmental persistence, and introduction of new materials.
665:
Unlike in most other substitution reactions, fluoride is the best leaving group, and iodide the worst. A 2018 paper indicates that this situation may actually be rather common, occurring in systems that were previously assumed to proceed via
228:
Aryl chlorides are the aryl halides produced on the largest scale commercially: 150,000 tons/y in the US alone (1994). Production levels are decreasing owing to environmental concerns. Chlorobenzenes are used mainly as solvents.
58:
because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.
590:) catalyze the reactions. Numerous are derivatives of electron-rich rings found in tyrosine, tryptophan, and various pyrroles. Some of these natural aryl halides exhibit useful medicinal properties.
629:
The C-X distances for aryl halides follow the expected trend. These distances for fluorobenzene, chlorobenzene, bromobenzene, and methyl 4-iodobenzoate are 135.6(4), 173.90(23), 189.8(1), and 209.9
445:
This method is applicable to the preparation of all aryl halides. One limitation is that most, but not all, aryl lithium and
Grignard reagents are produced from aryl halides.
363:
579:
Many chlorinated and brominated aromatic compounds are produced by marine organisms. The chloride and bromide in ocean waters are the source of the halogens. Various
768:, by adding the magnesium to the aryl halide in an ethereal solution, works well if the aromatic ring is not significantly deactivated by electron-withdrawing groups.
783:
The halides can be displaced by strong nucleophiles via reactions involving radical anions. Alternatively aryl halides, especially the bromides and iodides, undergo
646:
Unlike typical alkyl halides, aryl halides typically do not participate in conventional substitution reactions. Aryl halides with electron-withdrawing groups in the
1170:
Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Pyridine and
Pyridine Derivatives".
1205:
Mondal, Santanu; Raja, Karuppusamy; Schweizer, Ulrich; Mugesh, Govindasamy (2016). "Chemistry and
Biology in the Biosynthesis and Action of Thyroid Hormones".
920:
Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2002). "Fluorine
Compounds, Organic".
290:
conditions, whereas ring halogenation is favored in the presence of Lewis acids. The decolouration of bromine water by electron-rich arenes is used in the
1143:
Snieckus, Victor (1990). "Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics".
1172:
922:
1543:
sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene, dichlorobenzene and phenol as sole carbon sources".
72:
Aryl fluorides are used as synthetic intermediates, e.g. for the preparation of pharmaceuticals, pesticides, and liquid crystals. The conversion of
468:
includes halogenated derivatives of any aromatic compound, it commonly refers to halobenzenes, which are specifically halogenated derivatives of
409:, but otherwise these compounds are not produced on a large scale. Aryl iodides are "easy" substrates for many reactions such as
1240:
Brito, Juan P.; Ross, Joseph S.; El Kawkgi, Omar M.; Maraka, Spyridoula; Deng, Yihong; Shah, Nilay D.; Lipska, Kasia J. (2021).
1393:
1067:
1595:
1189:
984:
939:
393:
can also be used to convert diazonium salts to bromobenzenes using using copper-based reagents. Owing to high cost of
1100:
1009:
309:
of benzene has been well investigated, motivated by the avoidance of HCl as a coproduct in the direct halogenation:
350:
can also be used to convert diazonium salts to chlorobenzenes using copper-based reagents. Owing to high cost of
885:
Shimizu, Masaki; Hiyama, Tamejiro (2005). "Modern
Synthetic Methods for Fluorine-Substituted Target Molecules".
1002:
Electrophilic
HalogenationReaction Pathways Involving Attack by Electrophilic Halogens on Unsaturated Compounds
788:
76:
is a well established route to aryl fluorides. Thus, anilines are precursors to aryl fluorides. In the classic
390:
17:
420:
Aryl iodides can be prepared by treating diazonium salts with iodide salts. Electron-rich arenes such as
1622:
533:
492:
containing at least two different types of halogens bonded to the same benzene ring. There are also many
232:
967:
Beck, U.; Löser, E. (2011). "Chlorinated
Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons".
178:
721:
reaction, aryl halides are converted to aryl lithium compounds. Illustrative is the preparation of
1289:
410:
367:
417:, but they are much more expensive than the lighter, less reactive aryl chlorides and bromides.
1627:
811:
718:
493:
865:
371:
1587:
662:
reactions. For example, 2,4-dinitrochlorobenzene reacts in basic solution to give a phenol.
1487:
1422:
1350:
1341:
Gribble, Gordon W. (2004). "Natural
Organohalogens: A New Frontier for Medicinal Agents?".
406:
186:
182:
8:
1617:
1491:
1426:
1354:
1516:
1475:
1451:
1410:
1318:
1293:
1266:
1241:
829:
784:
771:
383:
347:
240:
77:
1474:
Jacobsen, Eric N.; Harrison A. Besser; Zeng, Yuwen; Kwan, Eugene E. (September 2018).
1591:
1560:
1521:
1503:
1456:
1438:
1389:
1323:
1271:
1222:
1185:
1096:
1063:
1031:
1005:
980:
935:
902:
717:, to give organometallic derivatives that function as sources of aryl anions. By the
489:
81:
43:
31:
1257:
1583:
1552:
1511:
1495:
1446:
1430:
1381:
1358:
1313:
1305:
1261:
1253:
1214:
1177:
1152:
1125:
1088:
1040:
972:
927:
894:
765:
549:
428:
414:
1385:
1092:
816:
587:
546:
375:
306:
278:
1556:
1309:
864:
Aryl bromides are widely used as fire-retardants. The most prominent member is
730:
509:
477:
473:
394:
351:
73:
1499:
1376:
Oberhammer, Heinz (2009). "The
Structural Chemistry of Carbon-Halogen Bonds".
1611:
1507:
1442:
1181:
1129:
1044:
976:
931:
722:
616:
517:
513:
481:
244:
174:
1564:
1525:
1460:
1327:
1275:
1226:
1218:
906:
898:
726:
683:
569:
485:
291:
287:
386:
is poorly reactive toward bromine, necessitating the use of acidic media.
802:. At high temperatures, aryl groups react with ammonia to give anilines.
529:
459:
236:
1434:
1156:
1083:
Lyday, Phyllis A.; Kaiho, Tatsuo (2015). "Iodine and Iodine
Compounds".
1362:
697:
602:
598:
580:
173:
Many commercial aryl fluorides are produced from aryl chlorides by the
55:
1409:
Ritter, Tobias; Hooker, Jacob M.; Neumann, Constanze N. (June 2016).
714:
630:
557:
516:. Chloropyridines are important intermediates to pharmaceuticals and
243:, catalyze the reactions. The most abundantly produced aryl halide,
615:
The chemical structure of 6,6′-dibromoindigo, the main component of
505:
47:
1473:
1025:
Atkinson, Edward R.; Murphy, Donald M.; Lufkin, James E. (1951). "
828:
declining since the 1980s, in part due to environmental concerns.
297:
27:
Aromatic compounds containing Halogen atom(s) in place of Hydrogen
1411:"Concerted nucleophilic aromatic substitution with 19F− and 18F−"
1169:
919:
710:
691:
687:
679:
469:
421:
283:
610:
572:
by electrophilic iodination of tyrosine derivative. Synthetic T
1057:
999:
799:
795:
583:
379:
301:
Reaction between benzene and halogen to form an halogenobenzene
277:
Monochlorination of benzene is accompanied by formation of the
51:
1116:
Janssen, Donald E.; Wilson, C. V. (1956). "4-Iodoveratrole".
593:
576:
is one of the most heavily prescribed medicines in the U.S.
177:. The method is often used for aryl chlorides also bearing
1578:
Ioffe, D.; Kampf, A. (2002). "Bromine, Organic Compounds".
868:, which is prepared by direct bromination of the diphenol.
655:
453:
46:
in which one or more hydrogen atoms, directly bonded to an
1204:
448:
1239:
235:
or "direct chlorination" is the main synthesis route.
424:
and dimethoxy derivatives react directly with iodine.
1062:. Englewood Cliffs, N.J: Prentice Hall. p. 947.
62:
1024:
1408:
1242:"Levothyroxine Use in the United States, 2008-2018"
704:
354:, this method is reserved for specialty chlorides.
397:, this method is reserved for specialty bromides.
678:Aryl halides often react via the intermediacy of
504:Halopyridines are based on the aromatic compound
362:The main aryl bromides produced commercially are
1609:
286:, the alkyl positions tend to be halogenated by
1580:Kirk-Othmer Encyclopedia of Chemical Technology
1476:"Concerted nucleophilic aromatic substitutions"
605:, is an aryl chloride isolated from soil fungi.
1173:Ullmann's Encyclopedia of Industrial Chemistry
1085:Ullmann's Encyclopedia of Industrial Chemistry
969:Ullmann's Encyclopedia of Industrial Chemistry
923:Ullmann's Encyclopedia of Industrial Chemistry
378:. They are produced by direct bromination of
1288:
1115:
884:
1538:
343:This technology is not widely used however.
523:
431:react with iodine to give the aryl halide:
1577:
1375:
1082:
1058:Boyd, Robert W.; Morrison, Robert (1992).
709:Aryl halides react with metals, generally
135:In some cases, the fluoride salt is used:
1515:
1450:
1317:
1265:
966:
962:
960:
958:
956:
954:
952:
540:
1142:
1000:Peter Bernard, David De la Mare (1976).
794:Chlorobenzene was once the precursor to
609:
592:
454:Halobenzenes and halobenzene derivatives
296:
1588:10.1002/0471238961.0218151325150606.a01
1340:
1294:"What's New in Enzymatic Halogenations"
1207:Angewandte Chemie International Edition
1051:
887:Angewandte Chemie International Edition
14:
1610:
1378:PATai's Chemistry of Functional Groups
1029:-4,4′,6,6′-Tetrachlorodiphenic Acid".
949:
528:Halogenated naphthalenes are based on
449:Classification according to aryl group
1539:Rehfuss, Marc; Urban, James (2005). "
798:, which is now made by oxidation of
624:
564:) are aryl iodides. A tetraiodide, T
181:. Illustrative is the synthesis of
1545:Systematic and Applied Microbiology
1298:Current Opinion in Chemical Biology
405:Synthetic aryl iodides are used as
24:
778:
770:
696:
63:Classification according to halide
25:
1639:
805:
472:. Groups of halobenzenes include
223:
67:
1292:; Walsh, Christopher T. (2007).
832:is produced from chlorobenzene:
705:Organometallic reagent formation
499:
357:
54:. Haloarenes are different from
1571:
1532:
1467:
1402:
1369:
1334:
1282:
1258:10.1001/jamainternmed.2021.2686
1233:
1198:
1163:
822:
641:
400:
374:. These materials are used as
1136:
1109:
1076:
1018:
1004:. Cambridge University Press.
993:
913:
878:
13:
1:
1386:10.1002/9780470682531.pat0002
1343:Journal of Chemical Education
1093:10.1002/14356007.a14_381.pub2
871:
815:is a bacterium that degrades
247:, is produced by this route:
636:
534:Polychlorinated naphthalenes
364:tetrabromophthalic anhydride
7:
1557:10.1016/j.syapm.2005.05.011
233:Friedel-Crafts halogenation
179:electron-withdrawing groups
10:
1644:
1310:10.1016/j.cbpa.2007.08.002
789:Buchwald–Hartwig amination
787:, and thus are subject to
673:
457:
1500:10.1038/s41557-018-0079-7
1290:Fujimori, Danica Galonić
1182:10.1002/14356007.a22_399
1130:10.15227/orgsyn.036.0046
1045:10.15227/orgsyn.031.0096
977:10.1002/14356007.o06_o03
932:10.1002/14356007.a11_349
819:as sole carbon sources.
524:Halogenated naphthalenes
411:cross-coupling reactions
1176:. Weinheim: Wiley-VCH.
926:. Weinheim: Wiley-VCH.
654:positions, can undergo
494:halobenzene derivatives
368:decabromodiphenyl ether
84:is the fluoride donor:
50:ring are replaced by a
1541:Rhodococcus phenolicus
1246:JAMA Internal Medicine
1219:10.1002/anie.201601116
899:10.1002/anie.200460441
812:Rhodococcus phenolicus
775:
719:metal-halogen exchange
701:
621:
607:
541:Aryl halides in nature
427:Aryl lithium and aryl
302:
866:tetrabromobisphenol-A
774:
700:
613:
596:
407:X-ray contrast agents
372:tetrabromobisphenol-A
300:
764:Direct formation of
682:. Chlorobenzene and
187:2-nitrochlorobenzene
183:2-fluoronitrobenzene
1492:2018NatCh..10..917K
1435:10.1038/nature17667
1427:2016Natur.534..369N
1355:2004JChEd..81.1441G
1157:10.1021/cr00104a001
1623:Aromatic compounds
1363:10.1021/ed081p1441
830:Triphenylphosphine
785:oxidative addition
776:
702:
622:
608:
490:mixed halobenzenes
464:Although the term
413:and conversion to
391:Gatterman reaction
384:Phthalic anhydride
382:and aryl ethers.
348:Gatterman reaction
303:
282:derivatives, e.g.
241:iron(III) chloride
78:Schiemann reaction
1421:(7607): 369–373.
1395:978-0-470-68253-1
1252:(10): 1402–1405.
1213:(27): 7606–7630.
1118:Organic Syntheses
1087:. pp. 1–13.
1069:978-0-13-643669-0
1060:Organic chemistry
1032:Organic Syntheses
791:-type reactions.
766:Grignard reagents
694:by this pathway.
625:Structural trends
429:Grignard reagents
415:Grignard reagents
206:Cl + KF → O
82:tetrafluoroborate
44:aromatic compound
32:organic chemistry
16:(Redirected from
1635:
1602:
1601:
1575:
1569:
1568:
1536:
1530:
1529:
1519:
1480:Nature Chemistry
1471:
1465:
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1454:
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1321:
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1202:
1196:
1195:
1167:
1161:
1160:
1145:Chemical Reviews
1140:
1134:
1133:
1113:
1107:
1106:
1080:
1074:
1073:
1055:
1049:
1047:
1022:
1016:
1015:
997:
991:
990:
964:
947:
945:
917:
911:
910:
882:
686:react in liquid
633:, respectively.
550:triiodothyronine
547:thyroid hormones
508:. This includes
441:
376:flame retardants
339:
273:
219:
169:
156:
155:
152:
131:
114:
113:
110:
105:
104:
101:
21:
1643:
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1407:
1403:
1396:
1374:
1370:
1339:
1335:
1287:
1283:
1238:
1234:
1203:
1199:
1192:
1168:
1164:
1141:
1137:
1114:
1110:
1103:
1081:
1077:
1070:
1056:
1052:
1023:
1019:
1012:
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987:
965:
950:
942:
918:
914:
883:
879:
874:
859:
855:
851:
847:
843:
839:
825:
817:dichlorobenzene
808:
781:
779:Other reactions
759:
755:
751:
747:
707:
676:
670:Ar mechanisms.
669:
659:
644:
639:
627:
620:
606:
601:, an important
588:bromoperoxidase
575:
567:
563:
555:
543:
526:
510:chloropyridines
502:
462:
456:
451:
440:→ ArI + LiI
439:
435:
403:
395:diazonium salts
360:
352:diazonium salts
337:
333:
329:
325:
321:
317:
313:
307:oxychlorination
279:dichlorobenzene
271:
267:
263:
259:
255:
251:
226:
217:
213:
209:
205:
201:
197:
193:
168:
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139:
130:
126:
122:
118:
111:
108:
107:
102:
99:
98:
96:
92:
88:
74:diazonium salts
70:
65:
38:(also known as
28:
23:
22:
15:
12:
11:
5:
1641:
1631:
1630:
1625:
1620:
1604:
1603:
1597:978-0471238966
1596:
1570:
1551:(8): 695–701.
1531:
1486:(9): 917–923.
1466:
1401:
1394:
1368:
1333:
1281:
1232:
1197:
1191:978-3527306732
1190:
1162:
1151:(6): 879–933.
1135:
1108:
1101:
1075:
1068:
1050:
1017:
1010:
992:
986:978-3527306732
985:
948:
941:978-3527306732
940:
912:
893:(2): 214–231.
876:
875:
873:
870:
862:
861:
857:
853:
849:
845:
841:
837:
824:
821:
807:
806:Biodegradation
804:
780:
777:
762:
761:
757:
753:
749:
745:
706:
703:
675:
672:
667:
657:
643:
640:
638:
635:
626:
623:
614:
597:
573:
570:biosynthesised
565:
561:
553:
542:
539:
525:
522:
514:bromopyridines
501:
498:
478:chlorobenzenes
474:fluorobenzenes
458:Main article:
455:
452:
450:
447:
443:
442:
437:
402:
399:
359:
356:
341:
340:
335:
331:
327:
323:
322:+ 4 HCl + O
319:
315:
275:
274:
269:
265:
261:
257:
253:
225:
224:Aryl chlorides
222:
221:
220:
215:
211:
207:
203:
199:
195:
171:
170:
166:
162:
158:
145:
141:
133:
132:
128:
124:
120:
116:
94:
90:
69:
68:Aryl fluorides
66:
64:
61:
26:
9:
6:
4:
3:
2:
1640:
1629:
1628:Organohalides
1626:
1624:
1621:
1619:
1616:
1615:
1613:
1599:
1593:
1589:
1585:
1581:
1574:
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1453:
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1436:
1432:
1428:
1424:
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1416:
1412:
1405:
1397:
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1387:
1383:
1379:
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1356:
1352:
1348:
1344:
1337:
1329:
1325:
1320:
1315:
1311:
1307:
1304:(5): 553–60.
1303:
1299:
1295:
1291:
1285:
1277:
1273:
1268:
1263:
1259:
1255:
1251:
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1102:9783527306732
1098:
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1061:
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1046:
1042:
1038:
1034:
1033:
1028:
1021:
1013:
1011:9780521290142
1007:
1003:
996:
988:
982:
978:
974:
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961:
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953:
943:
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916:
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869:
867:
835:
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833:
831:
820:
818:
814:
813:
803:
801:
797:
792:
790:
786:
773:
769:
767:
752:Br + BuLi → C
743:
742:
741:
739:
735:
734:-butyllithium
733:
728:
724:
723:phenyllithium
720:
716:
712:
699:
695:
693:
689:
685:
681:
671:
663:
661:
653:
649:
634:
632:
618:
617:Tyrian Purple
612:
604:
600:
595:
591:
589:
585:
582:
577:
571:
559:
551:
548:
538:
535:
531:
521:
519:
518:agrochemicals
515:
511:
507:
500:Halopyridines
497:
495:
491:
488:, as well as
487:
483:
482:bromobenzenes
479:
475:
471:
467:
461:
446:
434:
433:
432:
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423:
418:
416:
412:
408:
398:
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381:
377:
373:
369:
365:
358:Aryl bromides
355:
353:
349:
344:
312:
311:
310:
308:
299:
295:
293:
289:
285:
280:
250:
249:
248:
246:
245:chlorobenzene
242:
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192:
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184:
180:
176:
175:Halex process
138:
137:
136:
87:
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83:
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60:
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53:
49:
45:
41:
37:
33:
19:
1579:
1573:
1548:
1544:
1540:
1534:
1483:
1479:
1469:
1418:
1414:
1404:
1377:
1371:
1349:(10): 1441.
1346:
1342:
1336:
1301:
1297:
1284:
1249:
1245:
1235:
1210:
1206:
1200:
1171:
1165:
1148:
1144:
1138:
1121:
1117:
1111:
1084:
1078:
1059:
1053:
1036:
1030:
1026:
1020:
1001:
995:
968:
921:
915:
890:
886:
880:
863:
848:+ 6 Na → P(C
826:
823:Applications
810:
809:
793:
782:
763:
737:
731:
727:bromobenzene
708:
684:sodium amide
677:
664:
651:
647:
645:
642:Substitution
628:
578:
544:
527:
503:
486:iodobenzenes
465:
463:
444:
426:
419:
404:
401:Aryl iodides
388:
361:
345:
342:
304:
292:bromine test
288:free radical
276:
231:
227:
172:
134:
71:
39:
35:
29:
18:Aryl halides
760:Li + BuBr
530:naphthalene
466:aryl halide
460:Halobenzene
237:Lewis acids
56:haloalkanes
36:aryl halide
1618:Haloarenes
1612:Categories
872:References
603:antibiotic
599:Vancomycin
581:peroxidase
436:ArLi + I
272:Cl + HCl
1508:1755-4349
1443:1476-4687
715:magnesium
637:Reactions
558:thyroxine
218:F + KCl
157:]F → C
40:haloarene
1565:16261859
1526:30013193
1461:27281221
1328:17881282
1276:34152370
1227:27226395
907:15614922
860:+ 6 NaCl
844:Cl + PCl
740:-BuLi):
690:to give
680:benzynes
506:pyridine
422:anilines
334:Cl + H
48:aromatic
42:) is an
1517:6105541
1488:Bibcode
1452:4911285
1423:Bibcode
1351:Bibcode
1319:2151916
1267:8218227
711:lithium
692:aniline
688:ammonia
674:Benzyne
586:(e.g.,
584:enzymes
470:benzene
380:phenols
326:→ 4 C
284:toluene
239:, e.g.
165:F + N
123:F + N
1594:
1563:
1524:
1514:
1506:
1459:
1449:
1441:
1415:Nature
1392:
1326:
1316:
1274:
1264:
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1188:
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1099:
1066:
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1008:
983:
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800:cumene
796:phenol
729:using
556:) and
484:, and
370:, and
140:[C
89:[C
52:halide
725:from
648:ortho
264:→ C
260:+ Cl
185:from
127:+ BF
115:→ C
34:, an
1592:ISBN
1561:PMID
1522:PMID
1504:ISSN
1457:PMID
1439:ISSN
1390:ISBN
1324:PMID
1272:PMID
1223:PMID
1186:ISBN
1097:ISBN
1064:ISBN
1006:ISBN
981:ISBN
936:ISBN
903:PMID
652:para
650:and
545:The
512:and
389:The
346:The
305:The
1584:doi
1553:doi
1512:PMC
1496:doi
1447:PMC
1431:doi
1419:534
1382:doi
1359:doi
1314:PMC
1306:doi
1262:PMC
1254:doi
1250:181
1215:doi
1178:doi
1153:doi
1126:doi
1089:doi
1041:doi
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928:doi
895:doi
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713:or
568:is
314:4 C
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1211:55
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1037:31
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951:^
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891:44
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660:Ar
631:pm
560:(T
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532:.
520:.
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480:,
476:,
366:,
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210:NC
198:NC
189::
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930::
909:.
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854:5
852:H
850:6
846:3
842:5
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838:6
758:5
756:H
754:6
750:5
748:H
746:6
744:C
738:n
736:(
732:n
668:N
666:S
658:N
656:S
619:.
574:4
566:4
562:4
554:3
438:2
338:O
336:2
332:5
330:H
328:6
324:2
320:6
318:H
316:6
270:5
268:H
266:6
262:2
258:6
256:H
254:6
252:C
216:4
214:H
212:6
208:2
204:4
202:H
200:6
196:2
194:O
167:2
163:5
161:H
159:6
154:2
151:+
148:N
146:5
144:H
142:6
129:3
125:2
121:5
119:H
117:6
112:4
109:−
103:2
100:+
97:N
95:5
93:H
91:6
20:)
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