1029:
the fire safety of these materials. Its ability to suppress combustion effectively makes it a sought-after choice in industries concerned with fire prevention. However, its widespread application also leads to its dispersion in the environment. Additionally, HBB can undergo proto bromination reactions when treated with sodium methoxide in methanol and ethyl methyl ketone, yielding a mixture of tribromobenzene.Despite its efficacy in fire retardation, the environmental and health impacts of HBB underscore the importance of careful handling and monitoring in its utilization.
234:
159:
492:
655:
35:
1176:
658:
660:
1028:
Hexabromobenzene (HBB) finds extensive use as a fire retardant additive in a range of materials including plastics, paper, and electrical goods, where it serves as a top-tier flame retardant. With an impressive melting point of 327 °C and a high bromide content of 86%, HBB significantly enhances
1041:
hexabromobenzene also serves as one of the key polyhalogenated aromatic compounds used in the bottom-up synthesis process of graphene-like films. Through electrochemical reduction, HBB contributes to the formation of polyaromatic ring structures alongside other compounds like hexafluorobenzene (HFB)
1019:
Notably, the acute toxicity of HBB is observed to decrease with an increase in the number of bromine atoms in the molecule. However, the potential for necrotic changes varies based on the position of these bromine atoms within the molecule. There are severe health risks associated with HBB exposure,
1016:
for this hazard. Additionally, it induces skin and eye irritation, classified under category 2 for both. Moreover, HBB is known to cause skin sensitization (category 1) and specific target organ toxicity upon single exposure (category 3), with the respiratory system being the primary target organ.
1015:
Hexabromobenzene (HBB) poses significant dangers due to its toxicity profile as classified by the GHS (Globally
Harmonized System of Classification and Labeling of Chemicals). Classified as GHS07, HBB exhibits acute toxicity via oral, dermal, and inhalation routes, categorizing it under category 4
1045:
Hexabromobenzene (HBB) was utilized in a study investigating its metabolic fate in female rats, wherein the substance was orally administered at doses of 16.6 mg/kg body weight every other day for a span of 2 weeks. Analysis of the rats' excreta revealed the presence of various metabolites,
1037:
The influences of five organic cosolvents (acetone, methanol, ethanol, THF, or DMSO) on hexabromobenzene (HBB) degradation catalyzed by one typical reactive material montmorillonite-templated sub nanoscale zero-valent iron (CZVI) was investigated.The CZVI-catalyzed HBB degradation mechanism was
1229:
1101:
500:
472:
1193:
Kudaş, Züleyha; Gür, Emre; Ekinci, Duygu (11 June 2018). "Synthesis of
Graphene-like Films by Electrochemical Reduction of Polyhalogenated Aromatic Compounds and their Electrochemical Capacitor Applications".
919:
1042:
and hexachlorobenzene (HCB). It facilitates the creation of graphene-like carbon films upon thermal annealing, offering a cost-effective approach without the need for sophisticated equipment.
594:
1174:, Tsukasa Sato, Isao Fujiwara, Makoto Morita, Kenichi Horikawa, "High voltage capacitor and magnetron", published 2004-08-09, issued 2005-06-21, assigned to TDK Corp
659:
661:
669:
283:
590:
683:
116:
1344:"Influence of organic cosolvents on hexabromobenzene degradation in solution by montmorillonite-templated subnanoscale zero-valent iron"
936:
979:
of 327 °C. Whiteness percent of 93.0. Its bromine content is above 86%, and it represents high efficacy. Incompatible with strong
1155:
1125:
248:
578:
586:
820:
1038:
proposed as the electron transfer between zero-valent iron and HBB, which led to formation of four debromination products.
574:
741:
935:
The reaction to form
Hexabromobenzene, known as Bromination of Benzene, involves substitution of hydrogens by bromides.
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82:
1343:
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including unchanged HBB, penta bromobenzene, as well as oxygen- and sulfur-containing compounds.
815:) in the presence of a heat and UV light. This reaction is known as the bromination of Benzene:
558:
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1211:
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1121:
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1203:
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735:
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1020:
warranting careful handling and stringent safety measures in its use and management.
976:
761:
391:
359:
147:
1373:
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757:
562:
1374:"Premium 98% Pure Hexabromobenzene for Enhanced Fire Resistance & Versatility"
1359:
1280:
1207:
1071:
180:
940:
540:
402:
618:
34:
992:
939:
is a general method of derivatizing hexabromobenzene. Benzene is sufficiently
440:
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412:
398:
381:
328:
127:
532:
783:. It also has applications as a starting material in the formation of thin
776:
524:
1215:
955:
Hexabromobenzene is a white powder in physical form. It's not soluble in
784:
682:
675:
668:
641:
1342:
Peng, Anping; Gao, Hu; Wang, Huimin; Wang, Yi; Chen, Zeyou (July 2023).
1075:
1004:
996:
988:
968:
960:
947:
by bromide ions to give the substituted derivatives, hexabromobenzene.
808:
796:
769:
416:
387:
167:
923:
Apart from hexabromobenzene, the reaction produces six equivalents of
528:
17:
734:
Except where otherwise noted, data are given for materials in their
520:
1397:
Koss, G; Doring, H; Wurminghausen, B; Koransky, W (November 1982).
1256:"Benzene and Its Homologues: the Substitution Reactions of Benzene"
1120:(60 ed.). Boca Raton, Florida: CRC Press Inc. p. C-165.
1000:
984:
964:
956:
536:
115:
105:
676:
1150:. Vol. 1. Boca Raton, Florida: CRC Press Inc. p. 176.
787:-like films for low cost energy storage devices and capacitors.
630:
349:
610:
217:
897:
884:
868:
848:
835:
653:
983:. It has excellent integration flexibility with several
1260:
914:{\displaystyle {\ce {C6H6 + 6 Br2 -> C6Br6 + 6HBr}}}
823:
913:
1230:"18.1: Electrophilic Aromatic Substitution (EAS)"
179:
657:
91:
775:Hexabromobenzene has seen use in high voltage
8:
1399:"Metabolic fate of hexabromobenzene in rats"
1102:Institute for Occupational Safety and Health
257:InChI=1S/C6Br6/c7-1-2(8)4(10)6(12)5(11)3(1)9
1146:Weast, Robert C.; Astle, Melvin J. (1985).
267:InChI=1/C6Br6/c7-1-2(8)4(10)6(12)5(11)3(1)9
764:in which all six positions of the central
232:
157:
135:
26:
1148:CRC Handbook of Data On Organic Compounds
1141:
1139:
1137:
1067:
1065:
1063:
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834:
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824:
822:
199:
1111:
1109:
1089:
1087:
1085:
1083:
1055:
288:
253:
228:
364:327 °C (621 °F; 600 K)
148:
1337:
1335:
1320:from the original on January 13, 2024
1304:
1302:
1300:
260:Key: CAYGQBVSOZLICD-UHFFFAOYSA-N
7:
1188:
1186:
344:Monoclinic needles or white powder.
937:Electrophilic aromatic substitution
270:Key: CAYGQBVSOZLICD-UHFFFAOYAA
170:
25:
1118:Handbook of Chemistry and Physics
291:C1(=C(C(=C(C(=C1Br)Br)Br)Br)Br)Br
490:
33:
795:It can be prepared by reacting
738:(at 25 °C , 100 kPa).
318:
871:
312:
1:
1415:10.1016/0378-4274(82)90011-X
1360:10.1016/j.envres.2023.115986
1208:10.1021/acs.langmuir.8b01177
1451:
1262:, Elsevier, pp. 12–27
1254:TOMLINSON, MURIEL (1971),
1098:GESTIS Substance Database
732:
707:
471:
466:
376:0.16x10 mg/L (insoluble)
299:
279:
244:
75:
58:
46:
41:
32:
1285:pubchem.ncbi.nlm.nih.gov
807:) with 6 equivalents of
553:Precautionary statements
1348:Environmental Research
915:
760:and a six-substituted
664:
916:
663:
1234:Chemistry LibreTexts
1172:US Grant 6909590
1116:Weast, R.C. (1979).
821:
646:(fire diamond)
386:Slightly soluble in
48:Preferred IUPAC name
1316:. August 27, 2023.
995:in substances like
899:
886:
870:
850:
837:
371:Solubility in water
336: g·mol
29:
1403:Toxicology Letters
1378:Procurenet Limited
1310:"Hexabromobenzene"
1281:"Hexabromobenzene"
975:t is 551.7 g/mol.
959:but is soluble in
943:that it undergoes
911:
887:
874:
858:
838:
825:
742:Infobox references
708:Related compounds
665:
27:
1202:(27): 7958–7970.
909:
890:
877:
861:
841:
828:
750:Chemical compound
748:
747:
723:Hexachlorobenzene
719:Hexafluorobenzene
714:Related compounds
696:Safety data sheet
515:Hazard statements
213:CompTox Dashboard
117:Interactive image
28:Hexabromobenzene
16:(Redirected from
1442:
1419:
1418:
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1370:
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1179:
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1168:
1162:
1161:
1143:
1132:
1131:
1113:
1104:
1091:
1078:
1069:
981:oxidizing agents
925:Hydrogen Bromide
920:
918:
917:
912:
910:
907:
898:
895:
888:
885:
882:
875:
869:
866:
859:
849:
846:
839:
836:
833:
826:
768:are bonded to a
754:Hexabromobenzene
685:
678:
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628:
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494:
335:
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307:Chemical formula
237:
236:
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219:
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183:
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161:
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139:
119:
95:
52:Hexabromobenzene
37:
30:
21:
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1449:
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1444:
1443:
1441:
1440:
1439:
1425:
1424:
1423:
1422:
1396:
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1391:
1382:
1380:
1372:
1371:
1367:
1341:
1340:
1333:
1323:
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1308:
1307:
1298:
1289:
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1278:
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1273:
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1263:
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1252:
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1239:
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1228:
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1191:
1184:
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1165:
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1145:
1144:
1135:
1128:
1115:
1114:
1107:
1092:
1081:
1070:
1057:
1052:
1035:
1026:
1013:
973:Molecular weigh
953:
933:
819:
818:
814:
806:
802:
793:
781:flame retardant
751:
744:
739:
727:Hexaiodobenzene
725:
721:
715:
690:
689:
688:
687:
680:
673:
666:
662:
654:
555:
517:
503:
487:
445:Petroleum ether
373:
333:
323:
317:
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295:
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287:
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275:
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186:
173:
142:
122:
109:
98:
85:
71:
70:
64:Perbromobenzene
54:
53:
23:
22:
15:
12:
11:
5:
1448:
1446:
1438:
1437:
1427:
1426:
1421:
1420:
1409:(1–2): 69–77.
1389:
1365:
1331:
1296:
1271:
1246:
1221:
1182:
1163:
1156:
1133:
1126:
1105:
1079:
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1053:
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1048:
1034:
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1025:
1022:
1012:
1009:
952:
949:
932:
929:
905:
902:
894:
881:
873:
865:
856:
853:
845:
832:
812:
804:
800:
792:
789:
749:
746:
745:
740:
736:standard state
733:
730:
729:
716:
713:
710:
709:
705:
704:
699:
692:
691:
681:
674:
667:
652:
651:
650:
649:
647:
638:
637:
595:P305+P351+P338
556:
551:
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547:
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509:
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24:
14:
13:
10:
9:
6:
4:
3:
2:
1447:
1436:
1435:Bromobenzenes
1433:
1432:
1430:
1416:
1412:
1408:
1404:
1400:
1393:
1390:
1379:
1375:
1369:
1366:
1361:
1357:
1353:
1349:
1345:
1338:
1336:
1332:
1319:
1315:
1314:Sigma-Aldrich
1311:
1305:
1303:
1301:
1297:
1286:
1282:
1275:
1272:
1261:
1257:
1250:
1247:
1235:
1231:
1225:
1222:
1217:
1213:
1209:
1205:
1201:
1197:
1189:
1187:
1183:
1173:
1167:
1164:
1159:
1157:9780849304002
1153:
1149:
1142:
1140:
1138:
1134:
1129:
1127:9780849315565
1123:
1119:
1112:
1110:
1106:
1103:
1099:
1095:
1090:
1088:
1086:
1084:
1080:
1077:
1073:
1068:
1066:
1064:
1062:
1060:
1056:
1049:
1047:
1043:
1039:
1032:
1030:
1023:
1021:
1017:
1010:
1008:
1006:
1002:
998:
994:
990:
986:
982:
978:
977:Melting point
974:
970:
966:
962:
958:
950:
948:
946:
942:
938:
930:
928:
926:
921:
903:
900:
892:
879:
863:
854:
851:
843:
830:
816:
810:
798:
790:
788:
786:
782:
778:
773:
771:
767:
763:
759:
755:
743:
737:
731:
728:
724:
720:
717:
712:
711:
706:
703:
700:
697:
694:
693:
686:
679:
672:
648:
645:
644:
640:
639:
557:
554:
550:
549:
519:
516:
512:
511:
508:
505:
502:
498:
497:
493:
489:
486:
482:
481:
477:
475:
470:
465:
461:
459:
458:
453:
452:
448:
446:
442:
439:
438:
434:
432:
428:
425:
424:
420:
418:
414:
411:
410:
406:
404:
400:
397:
396:
393:
392:Diethyl ether
389:
385:
383:
380:
379:
375:
372:
368:
367:
363:
361:
360:Melting point
358:
357:
353:
351:
348:
347:
343:
340:
339:
332:
330:
327:
326:
311:
308:
304:
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298:
289:
285:
278:
264:
254:
250:
243:
235:
231:
230:DTXSID1024128
227:
226:
224:
214:
210:
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190:
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182:
178:
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175:
169:
165:
164:
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156:
153:
151:
149:ECHA InfoCard
146:
145:
138:
134:
133:
131:
129:
126:
125:
118:
114:
113:
111:
107:
102:
101:
94:
90:
89:
87:
84:
80:
79:
74:
66:
63:
62:
57:
49:
45:
40:
36:
31:
19:
1406:
1402:
1392:
1381:. Retrieved
1377:
1368:
1351:
1347:
1322:. Retrieved
1313:
1288:. Retrieved
1284:
1274:
1264:, retrieved
1259:
1249:
1238:. Retrieved
1236:. 2016-02-19
1233:
1224:
1199:
1195:
1166:
1147:
1117:
1044:
1040:
1036:
1033:Applications
1027:
1018:
1014:
954:
945:substitution
941:nucleophilic
934:
922:
817:
794:
774:
766:benzene ring
762:bromobenzene
758:aryl bromide
753:
752:
642:
506:
473:
456:
76:Identifiers
59:Other names
1324:February 3,
991:due to its
791:Preparation
501:Signal word
403:Acetic acid
341:Appearance
300:Properties
155:100.001.613
1383:2024-02-11
1354:: 115986.
1290:2024-02-11
1266:2024-02-11
1240:2024-02-11
1050:References
993:solubility
951:Properties
777:capacitors
485:Pictograms
441:Solubility
431:Chloroform
427:Solubility
413:Solubility
399:Solubility
382:Solubility
329:Molar mass
201:T01859XWIR
128:ChemSpider
104:3D model (
83:CAS Number
1279:PubChem.
872:⟶
702:LCSS 6905
627:P403+P233
615:P332+P313
591:P304+P340
587:P304+P312
583:P302+P352
579:P301+P312
476:labelling
354:Odorless
1429:Category
1318:Archived
1216:29890834
1196:Langmuir
1072:CID 6905
989:plastics
931:Reaction
785:graphene
643:NFPA 704
467:Hazards
407:Soluble
1100:of the
1096:in the
1094:Record
1076:PubChem
1011:Dangers
1005:benzene
997:ethanol
969:benzene
961:ethanol
927:(HBr).
809:bromine
797:benzene
770:bromine
417:Benzene
388:Ethanol
334:551.490
168:PubChem
93:87-82-1
1214:
1178:
1154:
1124:
1003:, and
985:resins
967:, and
772:atom.
756:is an
698:(SDS)
507:Danger
284:SMILES
42:Names
1074:from
1001:ether
965:ether
957:water
779:as a
462:6.07
249:InChI
106:JSmol
18:C6Br6
1326:2024
1212:PMID
1152:ISBN
1122:ISBN
1024:Uses
987:and
635:P501
631:P405
623:P363
619:P362
611:P330
607:P322
603:P321
599:P312
575:P280
571:P271
567:P270
563:P264
559:P261
545:H413
541:H335
537:H332
533:H319
529:H315
525:H312
521:H302
455:log
449:10%
435:10%
421:10%
350:Odor
192:UNII
181:6905
137:6639
1411:doi
1356:doi
1352:229
1204:doi
908:HBr
811:(Br
474:GHS
443:in
429:in
415:in
401:in
218:EPA
171:CID
67:HBB
1431::
1407:14
1405:.
1401:.
1376:.
1350:.
1346:.
1334:^
1312:.
1299:^
1283:.
1258:,
1232:.
1210:.
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