1018:
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.
223:
148:
481:
644:
24:
1165:
647:
649:
1017:
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
1030:
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)
1008:
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,
1005:
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.
1004:
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
1034:
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,
1026:
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
1218:
1090:
489:
461:
1182:
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".
908:
1031:
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.
583:
1163:, 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
648:
650:
658:
272:
579:
672:
105:
1333:"Influence of organic cosolvents on hexabromobenzene degradation in solution by montmorillonite-templated subnanoscale zero-valent iron"
925:
968:
of 327 °C. Whiteness percent of 93.0. Its bromine content is above 86%, and it represents high efficacy. Incompatible with strong
1144:
1114:
237:
567:
575:
809:
1027:
proposed as the electron transfer between zero-valent iron and HBB, which led to formation of four debromination products.
563:
730:
924:
The reaction to form
Hexabromobenzene, known as Bromination of Benzene, involves substitution of hydrogens by bromides.
541:
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1306:
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933:
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533:
36:
555:
218:
71:
1332:
1035:
including unchanged HBB, penta bromobenzene, as well as oxygen- and sulfur-containing compounds.
804:) in the presence of a heat and UV light. This reaction is known as the bromination of Benzene:
547:
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1110:
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684:
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913:
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81:
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1403:
1009:
warranting careful handling and stringent safety measures in its use and management.
965:
750:
380:
348:
136:
1362:
623:
754:
746:
551:
1363:"Premium 98% Pure Hexabromobenzene for Enhanced Fire Resistance & Versatility"
1348:
1269:
1196:
1060:
169:
929:
529:
391:
607:
23:
981:
928:
is a general method of derivatizing hexabromobenzene. Benzene is sufficiently
429:
419:
415:
401:
387:
370:
317:
116:
521:
772:. It also has applications as a starting material in the formation of thin
765:
513:
1204:
944:
Hexabromobenzene is a white powder in physical form. It's not soluble in
773:
671:
664:
657:
630:
1331:
Peng, Anping; Gao, Hu; Wang, Huimin; Wang, Yi; Chen, Zeyou (July 2023).
1064:
993:
985:
977:
957:
949:
936:
by bromide ions to give the substituted derivatives, hexabromobenzene.
797:
785:
758:
405:
376:
156:
912:
Apart from hexabromobenzene, the reaction produces six equivalents of
517:
723:
Except where otherwise noted, data are given for materials in their
509:
1386:
Koss, G; Doring, H; Wurminghausen, B; Koransky, W (November 1982).
1245:"Benzene and Its Homologues: the Substitution Reactions of Benzene"
1109:(60 ed.). Boca Raton, Florida: CRC Press Inc. p. C-165.
989:
973:
953:
945:
525:
104:
94:
665:
1139:. Vol. 1. Boca Raton, Florida: CRC Press Inc. p. 176.
776:-like films for low cost energy storage devices and capacitors.
619:
338:
599:
206:
886:
873:
857:
837:
824:
642:
972:. It has excellent integration flexibility with several
1249:
903:{\displaystyle {\ce {C6H6 + 6 Br2 -> C6Br6 + 6HBr}}}
812:
902:
1219:"18.1: Electrophilic Aromatic Substitution (EAS)"
168:
646:
80:
764:Hexabromobenzene has seen use in high voltage
8:
1388:"Metabolic fate of hexabromobenzene in rats"
1091:Institute for Occupational Safety and Health
246:InChI=1S/C6Br6/c7-1-2(8)4(10)6(12)5(11)3(1)9
1135:Weast, Robert C.; Astle, Melvin J. (1985).
256:InChI=1/C6Br6/c7-1-2(8)4(10)6(12)5(11)3(1)9
753:in which all six positions of the central
221:
146:
124:
15:
1137:CRC Handbook of Data On Organic Compounds
1130:
1128:
1126:
1056:
1054:
1052:
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813:
811:
188:
1100:
1098:
1078:
1076:
1074:
1072:
1044:
277:
242:
217:
353:327 °C (621 °F; 600 K)
137:
1326:
1324:
1309:from the original on January 13, 2024
1293:
1291:
1289:
249:Key: CAYGQBVSOZLICD-UHFFFAOYSA-N
7:
1177:
1175:
333:Monoclinic needles or white powder.
926:Electrophilic aromatic substitution
259:Key: CAYGQBVSOZLICD-UHFFFAOYAA
159:
14:
1107:Handbook of Chemistry and Physics
280:C1(=C(C(=C(C(=C1Br)Br)Br)Br)Br)Br
479:
22:
784:It can be prepared by reacting
727:(at 25 °C , 100 kPa).
307:
860:
301:
1:
1404:10.1016/0378-4274(82)90011-X
1349:10.1016/j.envres.2023.115986
1197:10.1021/acs.langmuir.8b01177
1440:
1251:, Elsevier, pp. 12–27
1243:TOMLINSON, MURIEL (1971),
1087:GESTIS Substance Database
721:
696:
460:
455:
365:0.16x10 mg/L (insoluble)
288:
268:
233:
64:
47:
35:
30:
21:
1274:pubchem.ncbi.nlm.nih.gov
796:) with 6 equivalents of
542:Precautionary statements
1337:Environmental Research
904:
749:and a six-substituted
653:
905:
652:
1223:Chemistry LibreTexts
1161:US Grant 6909590
1105:Weast, R.C. (1979).
810:
635:(fire diamond)
375:Slightly soluble in
37:Preferred IUPAC name
1305:. August 27, 2023.
984:in substances like
888:
875:
859:
839:
826:
360:Solubility in water
325: g·mol
18:
1392:Toxicology Letters
1367:Procurenet Limited
1299:"Hexabromobenzene"
1270:"Hexabromobenzene"
964:t is 551.7 g/mol.
948:but is soluble in
932:that it undergoes
900:
876:
863:
847:
827:
814:
731:Infobox references
697:Related compounds
654:
16:
1191:(27): 7958–7970.
898:
879:
866:
850:
830:
817:
739:Chemical compound
737:
736:
712:Hexachlorobenzene
708:Hexafluorobenzene
703:Related compounds
685:Safety data sheet
504:Hazard statements
202:CompTox Dashboard
106:Interactive image
17:Hexabromobenzene
1431:
1408:
1407:
1383:
1377:
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1353:
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1328:
1319:
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1314:
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1209:
1208:
1179:
1170:
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1168:
1164:
1157:
1151:
1150:
1132:
1121:
1120:
1102:
1093:
1080:
1067:
1058:
970:oxidizing agents
914:Hydrogen Bromide
909:
907:
906:
901:
899:
896:
887:
884:
877:
874:
871:
864:
858:
855:
848:
838:
835:
828:
825:
822:
815:
757:are bonded to a
743:Hexabromobenzene
674:
667:
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324:
309:
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296:Chemical formula
226:
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128:
108:
84:
41:Hexabromobenzene
26:
19:
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1428:
1414:
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1412:
1411:
1385:
1384:
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1369:
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1330:
1329:
1322:
1312:
1310:
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1262:
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1242:
1241:
1237:
1228:
1226:
1217:
1216:
1212:
1181:
1180:
1173:
1166:
1159:
1158:
1154:
1147:
1134:
1133:
1124:
1117:
1104:
1103:
1096:
1081:
1070:
1059:
1046:
1041:
1024:
1015:
1002:
962:Molecular weigh
942:
922:
808:
807:
803:
795:
791:
782:
770:flame retardant
740:
733:
728:
716:Hexaiodobenzene
714:
710:
704:
679:
678:
677:
676:
669:
662:
655:
651:
643:
544:
506:
492:
476:
434:Petroleum ether
362:
322:
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306:
298:
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162:
131:
111:
98:
87:
74:
60:
59:
53:Perbromobenzene
43:
42:
12:
11:
5:
1437:
1435:
1427:
1426:
1416:
1415:
1410:
1409:
1398:(1–2): 69–77.
1378:
1354:
1320:
1285:
1260:
1235:
1210:
1171:
1152:
1145:
1122:
1115:
1094:
1068:
1043:
1042:
1040:
1037:
1023:
1020:
1014:
1011:
1001:
998:
941:
938:
921:
918:
894:
891:
883:
870:
862:
854:
845:
842:
834:
821:
801:
793:
789:
781:
778:
738:
735:
734:
729:
725:standard state
722:
719:
718:
705:
702:
699:
698:
694:
693:
688:
681:
680:
670:
663:
656:
641:
640:
639:
638:
636:
627:
626:
584:P305+P351+P338
545:
540:
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477:
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3:
2:
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1425:
1424:Bromobenzenes
1422:
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1419:
1405:
1401:
1397:
1393:
1389:
1382:
1379:
1368:
1364:
1358:
1355:
1350:
1346:
1342:
1338:
1334:
1327:
1325:
1321:
1308:
1304:
1303:Sigma-Aldrich
1300:
1294:
1292:
1290:
1286:
1275:
1271:
1264:
1261:
1250:
1246:
1239:
1236:
1224:
1220:
1214:
1211:
1206:
1202:
1198:
1194:
1190:
1186:
1178:
1176:
1172:
1162:
1156:
1153:
1148:
1146:9780849304002
1142:
1138:
1131:
1129:
1127:
1123:
1118:
1116:9780849315565
1112:
1108:
1101:
1099:
1095:
1092:
1088:
1084:
1079:
1077:
1075:
1073:
1069:
1066:
1062:
1057:
1055:
1053:
1051:
1049:
1045:
1038:
1036:
1032:
1028:
1021:
1019:
1012:
1010:
1006:
999:
997:
995:
991:
987:
983:
979:
975:
971:
967:
966:Melting point
963:
959:
955:
951:
947:
939:
937:
935:
931:
927:
919:
917:
915:
910:
892:
889:
881:
868:
852:
843:
840:
832:
819:
805:
799:
787:
779:
777:
775:
771:
767:
762:
760:
756:
752:
748:
744:
732:
726:
720:
717:
713:
709:
706:
701:
700:
695:
692:
689:
686:
683:
682:
675:
668:
661:
637:
634:
633:
629:
628:
546:
543:
539:
538:
508:
505:
501:
500:
497:
494:
491:
487:
486:
482:
478:
475:
471:
470:
466:
464:
459:
454:
450:
448:
447:
442:
441:
437:
435:
431:
428:
427:
423:
421:
417:
414:
413:
409:
407:
403:
400:
399:
395:
393:
389:
386:
385:
382:
381:Diethyl ether
378:
374:
372:
369:
368:
364:
361:
357:
356:
352:
350:
349:Melting point
347:
346:
342:
340:
337:
336:
332:
329:
328:
321:
319:
316:
315:
300:
297:
293:
292:
287:
278:
274:
267:
253:
243:
239:
232:
224:
220:
219:DTXSID1024128
216:
215:
213:
203:
199:
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191:
187:
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184:
182:
179:
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171:
167:
166:
164:
158:
154:
153:
149:
145:
142:
140:
138:ECHA InfoCard
135:
134:
127:
123:
122:
120:
118:
115:
114:
107:
103:
102:
100:
96:
91:
90:
83:
79:
78:
76:
73:
69:
68:
63:
55:
52:
51:
46:
38:
34:
29:
25:
20:
1395:
1391:
1381:
1370:. Retrieved
1366:
1357:
1340:
1336:
1311:. Retrieved
1302:
1277:. Retrieved
1273:
1263:
1253:, retrieved
1248:
1238:
1227:. Retrieved
1225:. 2016-02-19
1222:
1213:
1188:
1184:
1155:
1136:
1106:
1033:
1029:
1025:
1022:Applications
1016:
1007:
1003:
943:
934:substitution
930:nucleophilic
923:
911:
806:
783:
763:
755:benzene ring
751:bromobenzene
747:aryl bromide
742:
741:
631:
495:
462:
445:
65:Identifiers
48:Other names
1313:February 3,
980:due to its
780:Preparation
490:Signal word
392:Acetic acid
330:Appearance
289:Properties
144:100.001.613
1372:2024-02-11
1343:: 115986.
1279:2024-02-11
1255:2024-02-11
1229:2024-02-11
1039:References
982:solubility
940:Properties
766:capacitors
474:Pictograms
430:Solubility
420:Chloroform
416:Solubility
402:Solubility
388:Solubility
371:Solubility
318:Molar mass
190:T01859XWIR
117:ChemSpider
93:3D model (
72:CAS Number
1268:PubChem.
861:⟶
691:LCSS 6905
616:P403+P233
604:P332+P313
580:P304+P340
576:P304+P312
572:P302+P352
568:P301+P312
465:labelling
343:Odorless
1418:Category
1307:Archived
1205:29890834
1185:Langmuir
1061:CID 6905
978:plastics
920:Reaction
774:graphene
632:NFPA 704
456:Hazards
396:Soluble
1089:of the
1085:in the
1083:Record
1065:PubChem
1000:Dangers
994:benzene
986:ethanol
958:benzene
950:ethanol
916:(HBr).
798:bromine
786:benzene
759:bromine
406:Benzene
377:Ethanol
323:551.490
157:PubChem
82:87-82-1
1203:
1167:
1143:
1113:
992:, and
974:resins
956:, and
761:atom.
745:is an
687:(SDS)
496:Danger
273:SMILES
31:Names
1063:from
990:ether
954:ether
946:water
768:as a
451:6.07
238:InChI
95:JSmol
1315:2024
1201:PMID
1141:ISBN
1111:ISBN
1013:Uses
976:and
624:P501
620:P405
612:P363
608:P362
600:P330
596:P322
592:P321
588:P312
564:P280
560:P271
556:P270
552:P264
548:P261
534:H413
530:H335
526:H332
522:H319
518:H315
514:H312
510:H302
444:log
438:10%
424:10%
410:10%
339:Odor
181:UNII
170:6905
126:6639
1400:doi
1345:doi
1341:229
1193:doi
897:HBr
800:(Br
463:GHS
432:in
418:in
404:in
390:in
207:EPA
160:CID
56:HBB
1420::
1396:14
1394:.
1390:.
1365:.
1339:.
1335:.
1323:^
1301:.
1288:^
1272:.
1247:,
1221:.
1199:.
1189:34
1187:.
1174:^
1125:^
1097:^
1071:^
1047:^
996:.
988:,
960:.
952:,
878:Br
849:Br
788:(C
622:,
618:,
614:,
610:,
606:,
602:,
598:,
594:,
590:,
586:,
582:,
578:,
574:,
570:,
566:,
562:,
558:,
554:,
550:,
532:,
528:,
524:,
520:,
516:,
512:,
467::
379:,
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1406:.
1402::
1375:.
1351:.
1347::
1317:.
1282:.
1232:.
1207:.
1195::
1149:.
1119:.
893:6
890:+
882:6
869:6
865:C
853:2
844:6
841:+
833:6
829:H
820:6
816:C
802:2
794:6
792:H
790:6
673:0
666:0
659:2
446:P
311:6
305:6
302:C
209:)
205:(
97:)
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