902:
305:
196:
33:
808:
24:
529:
534:
1009:
939:
687:
917:
or developing solutions, and as a reagent for the analytical determination of silver. More importantly, it has been extensively used as a corrosion inhibitor in the atmosphere and underwater. Also, its derivatives and their effectiveness as drug precursors have been drawing attention. Besides all the
930:
Benzotriazole is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions. It is known that a passive layer, consisting of a complex between copper and benzotriazole, is formed when copper is immersed in a solution containing benzotriazole. The passive
840:
Not only can it act either as an acid or base, it can also bind to other species, utilizing the lone pair electrons. Applying this property, the BTA can form a stable coordination compound on a copper surface and behave as a corrosion inhibitor.
931:
layer is insoluble in aqueous and many organic solutions. There is a positive correlation between the thickness of the passive layer and the efficiency of preventing corrosion. BTA is used in heritage conservation, notably for the treatment of
542:
509:
967:
have useful inhibitory properties against different proteins. Benzotriazole esters are used as mechanism-based inactivators to treat severe acute respiratory syndrome (SARS) by inhibiting the SARS 3CL protease of the
769:
984:
and a substantial fraction reaches surface water such as rivers and lakes. It is considered to be of low toxicity and a low health hazard to humans although exhibiting some antiestrogenic properties.
1472:
Farré, Marinel la; Pérez, Sandra; Kantiani, Lina; Barceló, Damià (2008). "Fate and toxicity of emerging pollutants, their metabolites and transformation products in the aquatic environment".
999:
that differ from benzotriazole by the addition of one methyl group attached somewhere on the benzene ring. Tolyltriazole has similar uses, but has better solubility in some organic solvents.
628:
700:
901:
959:
have chemical and biological properties that are versatile in the pharmaceutical industry. Benzotriazole derivatives act as agonists for many proteins. For instance,
1522:
768:
354:
1027:
624:
1309:
Katritzky, Alan R.; Wang, Zuoquan; Lang, Hengyuan (1996). "Novel and
Convenient Synthesis of Aroyl-, Heteroaroyl-, Alkenoyl-, and Alkynoylsilanes".
1437:
Giger, W; Schaffner, C; Kohler, HP (2006). "Benzotriazole and tolyltriazole as aquatic contaminants. 1. Input and occurrence in rivers and lakes".
972:
virus. The methodology is not only limited to heterocyclization but was also successful for polynuclear hydrocarbons of small carbocyclic systems.
738:. Its five-membered ring contains three consecutive nitrogen atoms. This bicyclic compound may be viewed as fused rings of the aromatic compounds
1109:
980:
Benzotriazole is fairly water-soluble, not readily degradable and has a limited sorption tendency. Hence, it is only partly removed in
1054:
319:
1532:
844:
Benzotriazole (BtH) reacts with aromatic aldehydes (ArCHO) in the presence of ethanol to give benzotriazole-based N,O-acetals:
814:
The synthesis can be improved when the reaction is carried out at low temperatures (5–10 °C) and briefly irradiated in an
807:
616:
620:
913:
Benzotriazole has been known for its great versatility. It has already been used as a restrainer (or anti-fogging agent) in
1527:
873:
612:
1398:"Recent developments in benzotriazole methodology for construction of pharmacologically important heterocyclic skeletons"
707:
586:
262:
533:
283:
528:
486:
468:
1517:
203:
1031:
1074:
Katritzky, A. R.; Rachwal S.; Hitchings G. J. (14 January 1991). "Benzotriazole: A novel synthetic auxiliary".
1013:
640:
1512:
1369:
Finšgar, M.; Milošev I. (11 March 2010). "Inhibition of copper corrosion by 1,2,3-benzotriazole: A review".
632:
191:
956:
935:. The exact structure of the copper-BTA complex is controversial and many proposals have been suggested.
914:
723:
556:
521:
153:
113:
996:
943:
45:
747:
600:
300:
79:
1340:(1969). "Reactive intermediates. Part I. Synthesis and oxidation of 1- and 2-aminobenzotriazole".
1419:
1191:
784:
592:
578:
946:
from benzotriazolate and copper(I), the active ingredient in the BT-derived corrosion inhibition
863:
775:
Various structural analyses with UV, IR and H-NMR spectra indicate that tautomer A is dominant.
918:
applications mentioned above, the BTA can be used as antifreezes, heating and cooling systems,
604:
574:
1489:
1454:
1277:
1120:
889:
1257:
1256:
Pereira, Claudio M. P.; Stefani, Helio A.; Guzen, Karla P.; Orfao, Aline T. G. (2007-07-31).
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1342:
1058:
919:
815:
173:
23:
1258:"Improved Synthesis of Benzotriazoles and 1-Acylbenzotriazoles by Ultrasound Irradiation"
1051:
758:
Benzotriazole features two fused rings. Its five-membered ring can in principle exist as
304:
195:
133:
89:
932:
791:
678:
1087:
1506:
1396:
Kale, Raju R.; Virendra Prasad; Prabhu P. Mohapatra; Vinod K. Tiwari (6 March 2010).
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1069:
1067:
1458:
1273:
1169:
1167:
1165:
1008:
746:. This white-to-light tan solid has a variety of uses, for instance, as a
1355:
1174:
Sease, Catherine (May 1978). "Benzotriazole: A Review for
Conservators".
960:
759:
743:
1195:
938:
885:
739:
426:
222:
204:
1450:
1322:
144:
1187:
677:
Except where otherwise noted, data are given for materials in their
562:
1229:
Damschroder, R. E.; Peterson, W. D. (1940). "1,2,3-Benzotriazole".
937:
570:
246:
124:
112:
102:
858:
These acetals are susceptible to deprotonation, giving access to
644:
1103:
1101:
1099:
1097:
636:
288:
1119:. Florida Center for Heterocyclic Compounds. Archived from
880:
gives 1-aminobenzotriazole. Oxidation of this amine with
1296:"Benzotriazole - Chemical Supplier Distributor Chemceed"
695:
328:
InChI=1S/C6H5N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H,(H,7,8,9)
1208:
338:
InChI=1/C6H5N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H,(H,7,8,9)
783:
Synthesis of benzotriazole involves the reaction of
849:ArCHO + BtH + EtOH → ArCH(OEt)(Bt) + H
234:
88:
1210:Ullmann's Encyclopedia of Industrial Chemistry
1146:"1,2,3-BENZOTRIAZOLE | CAMEO Chemicals | NOAA"
1117:Lecture presented at various locations in 2002
67:-Benzotriazole; 1,2,3-Benzotriazole; BTA; BtaH
8:
818:. Typical batch purity is 98.5% or greater.
303:
194:
172:
15:
1413:
270:
850:
1019:
833:It is a very weak Brønsted base with pK
359:
324:
299:
1523:Conservation and restoration materials
1439:Environmental Science & Technology
922:, and vapor-phase inhibitors as well.
451:350 °C (662 °F; 623 K)
441:100 °C (212 °F; 373 K)
185:
1047:
1045:
1043:
331:Key: QRUDEWIWKLJBPS-UHFFFAOYSA-N
152:
132:
7:
1474:TrAC Trends in Analytical Chemistry
341:Key: QRUDEWIWKLJBPS-UHFFFAOYAH
225:
14:
1028:"1H-Benzotriazole (CAS 95-14-7)"
1007:
900:
806:
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685:
532:
527:
395:
389:
31:
22:
1110:"Adventures with Benzotriazole"
681:(at 25 °C , 100 kPa).
798:. The conversion proceeds via
383:
1:
1212:, 2002, Wiley-VCH, Weinheim.
1088:10.1016/S0040-4020(01)87080-0
1383:10.1016/j.corsci.2010.05.002
826:BTA is a weak acid with a pK
802:of one of the amine groups:
1057:September 27, 2007, at the
995:is a mixture of isomers or
982:wastewater treatment plants
726:with the chemical formula C
1549:
1486:10.1016/j.trac.2008.09.010
942:Chemical structure of the
1415:10.1007/s00706-010-0378-1
675:
654:
508:
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370:
350:
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72:
60:
44:
39:
30:
21:
1243:10.15227/orgsyn.020.0016
1218:10.1002/14356007.a19_405
587:Precautionary statements
1176:Studies in Conservation
1150:cameochemicals.noaa.gov
1061:, SRC PhysProp Database
976:Environmental relevance
872:-amination of BtH with
779:Synthesis and reactions
1533:Photographic chemicals
1274:10.1002/chin.200731104
947:
915:photographic emulsions
1016:at Wikimedia Commons
941:
724:heterocyclic compound
1528:Corrosion inhibitors
1356:10.1039/J39690000742
1082:(16–17): 2683–2732.
944:coordination polymer
926:Corrosion inhibition
837: < 0.
54:-1,2,3-Benzotriazole
46:Preferred IUPAC name
748:corrosion inhibitor
458:Solubility in water
413: g·mol
18:
948:
830: = 8.2
708:Infobox references
655:Related compounds
16:
1451:10.1021/es061565j
1408:(11): 1159–1182.
1402:Monatsh Chemistry
1371:Corrosion Science
1323:10.1021/om950712b
1231:Organic Syntheses
1108:Katritzky, A. R.
1012:Media related to
988:Related compounds
788:-phenylenediamine
716:Chemical compound
714:
713:
661:Related compounds
557:Hazard statements
284:CompTox Dashboard
114:Interactive image
1540:
1518:Chelating agents
1498:
1497:
1480:(11): 991–1007.
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1428:
1427:
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1377:(9): 2737–2749.
1366:
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1336:Campbell, C.D.;
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1126:on 26 April 2012
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1071:
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1052:1H-Benzotriazole
1049:
1038:
1035:
1030:. Archived from
1024:
1011:
920:hydraulic fluids
904:
888:, which rapidly
882:lead(IV) acetate
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1445:(23): 7186–92.
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1343:J. Chem. Soc. C
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816:ultrasonic bath
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1513:Benzotriazoles
1505:
1504:
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1429:
1388:
1361:
1350:(5): 742–747.
1328:
1317:(2): 486–490.
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1034:on 2020-10-24.
1018:
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1001:
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955:Benzotriazole
952:
951:Drug precursor
949:
933:bronze disease
927:
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910:
907:
906:
905:
878:-sulfonic acid
874:hydroxylamine-
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629:P305+P351+P338
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17:Benzotriazole
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1014:Benzotriazole
1010:
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993:Tolyltriazole
987:
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800:diazotization
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749:
745:
741:
725:
721:
720:Benzotriazole
709:
702:
697:
680:
674:
671:
670:Tolyltriazole
667:
666:Benzimidazole
664:
659:
658:
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591:
588:
584:
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1182:(2): 76–85.
1179:
1175:
1153:. Retrieved
1149:
1140:
1128:. Retrieved
1121:the original
1116:
1079:
1075:
1036:
1032:the original
1022:
1006:
991:
979:
954:
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912:
909:Applications
875:
869:
868:
857:
843:
839:
832:
825:
813:
785:
782:
774:
757:
750:for copper.
719:
718:
548:
510:
490:
472:
421:White solid
362:n1c2ccccc2n1
247:RTECS number
73:Identifiers
64:
61:Other names
51:
1130:23 November
1076:Tetrahedron
957:derivatives
894:biphenylene
864:acylboranes
860:acylsilanes
796:acetic acid
722:(BTA) is a
543:Signal word
418:Appearance
371:Properties
192:100.002.177
154:ChEMBL84963
134:CHEBI:75331
1507:Categories
1338:Rees, C.W.
1262:ChemInform
1155:2023-01-17
1003:References
970:SARS-CoV-1
965:alizapride
522:Pictograms
431:1.36 g/mL
406:Molar mass
272:86110UXM5Y
165:ChemSpider
101:3D model (
80:CAS Number
1494:0165-9936
1282:0931-7597
997:congeners
890:dimerises
822:Reactions
760:tautomers
754:Structure
641:P337+P313
625:P304+P340
621:P304+P312
617:P301+P312
513:labelling
254:DM1225000
213:202-394-1
205:EC Number
1459:17180965
1424:93911988
1055:Archived
961:vorozole
884:affords
762:A and B:
744:triazole
504:Hazards
499:> 14
487:Basicity
1196:1505798
886:benzyne
740:benzene
701:what is
699: (
549:Warning
469:Acidity
463:20 g/L
427:Density
411:119.127
223:PubChem
90:95-14-7
1492:
1457:
1422:
1280:
1268:(31).
1237:: 16.
1194:
794:, and
696:verify
693:
355:SMILES
145:ChEMBL
40:Names
1420:S2CID
1192:JSTOR
1178:. 2.
1124:(PDF)
1113:(PDF)
320:InChI
125:ChEBI
103:JSmol
1490:ISSN
1455:PMID
1348:1969
1278:ISSN
1132:2011
963:and
862:and
742:and
649:P501
645:P391
637:P330
633:P312
613:P280
609:P273
605:P271
601:P270
597:P264
593:P261
579:H412
575:H411
571:H332
567:H319
563:H302
481:8.2
263:UNII
236:7220
174:6950
1482:doi
1447:doi
1410:doi
1406:141
1379:doi
1352:doi
1319:doi
1270:doi
1239:doi
1214:doi
1184:doi
1084:doi
892:to
511:GHS
289:EPA
226:CID
1509::
1488:.
1478:27
1476:.
1453:.
1443:40
1441:.
1418:.
1404:.
1400:.
1375:52
1373:.
1346:.
1315:15
1313:.
1276:.
1266:38
1264:.
1260:.
1235:20
1233:.
1190:.
1180:23
1164:^
1148:.
1115:.
1096:^
1080:47
1078:.
1066:^
1042:^
896:.
866:.
790:,
668:,
647:,
643:,
639:,
635:,
631:,
627:,
623:,
619:,
615:,
611:,
607:,
603:,
599:,
595:,
577:,
573:,
569:,
565:,
515::
496:)
489:(p
478:)
471:(p
1496:.
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1461:.
1449::
1426:.
1412::
1385:.
1381::
1358:.
1354::
1325:.
1321::
1298:.
1284:.
1272::
1245:.
1241::
1216::
1198:.
1186::
1158:.
1134:.
1090:.
1086::
876:O
870:N
853:O
851:2
835:a
828:a
786:o
736:3
734:N
732:5
730:H
728:6
691:N
494:b
491:K
476:a
473:K
399:3
396:N
393:5
390:H
387:6
384:C
291:)
287:(
105:)
65:H
63:1
52:H
50:1
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