40:
49:
352:
243:
658:
785:
31:
902:
788:
790:
789:
666:
638:
1285:
Wadkins. R. M. et al "Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J. Med. Chem., 2005 48 pp 2906–15.
1002:, which indicates the absence of pi-bonding between the two carbonyl centers. The PhCO centers are planar, but the pair of benzoyl groups are twisted with respect to the other with a
1232:
Quang. Shen, Kolbjoern. Hagen "Gas-phase molecular structure and conformation of benzil as determined by electron diffraction" J. Phys. Chem., 1987, 91 (6), pp 1357–1360.
732:
791:
799:
915:
813:
401:
1216:
Hardo Siegel, Manfred
Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Weinheim.
806:
728:
1046:
radiation at a wavelength of 260 nm, leading to decomposition with formation of free-radical species and formation of
1254:
148:
141:
1295:
Depreux, P.; Bethegnies, G.; Marcincal-Lefebvre, A. (1988). "Synthesis of benzil from benzoin with copper(II) acetate".
1059:
1332:"One-Pot Synthesis Benzils from Aldehydes Via Nhc-Catalyzed Benzoin Dimerization Under Metal-Free Conditions in Water"
1264:
366:
922:
910:
617:
73:
1118:
702:
309:
238:
1098:
330:
200:
720:
1130:
1050:
within the material. However, it is a relatively poor photoinitiator, and is seldom used. It undergoes
657:
1368:
250:
1203:
756:
347:
563:
680:
650:
39:
748:
1304:
1054:, which allows the curing light to reach deeper layers of the material on longer exposure.
744:
318:
61:
736:
220:
48:
8:
117:
107:
1308:
351:
242:
180:
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1312:
1233:
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1070:
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1007:
945:
509:
429:
1110:
597:
282:
1051:
1003:
979:
893:
708:
839:
1362:
1221:
1102:
1077:
involved in the hydrolysis of carboxylesters and many clinically used drugs.
716:
538:
498:
488:
231:
1330:
Bi, Xiaoxin; Wu, Lintao; Yan, Chaoguo; Jing, Xiaobi; Zhu, Hongxiang (2011).
876:
812:
1146:
1043:
1019:
740:
1237:
798:
724:
30:
1163:) can be used as an inexpensive catalyst for this chemical conversion.
1047:
805:
631:
548:
534:
520:
457:
251:
211:
1316:
503:
346.0 to 348.0 °C; 654.8 to 658.4 °F; 619.1 to 621.1 K
375:
InChI=1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H
1106:
385:
InChI=1/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H
892:
Except where otherwise noted, data are given for materials in their
493:
94.0 to 96.0 °C; 201.2 to 204.8 °F; 367.1 to 369.2 K
1294:
1015:
999:
975:
959:
884:
864:
858:
771:
764:
147:
140:
1090:
1039:
1011:
880:
712:
552:
524:
478:
269:
1034:
Most benzil can be used as a photoinitiator in the free-radical
1074:
1055:
967:
949:
944:, systematically known as 1,2-diphenylethane-1,2-dione) is the
191:
17:
1105:. This reactivity is exploited in the preparation of the drug
994:
The compound's most noteworthy structural feature is the long
694:
752:
604:
293:
171:
130:
335:
690:
1141:
PhC(O)CH(OH)Ph + 2 Cu → PhC(O)C(O)Ph + 2 H + 2 Cu
1101:, in which base catalyses the conversion of benzil to
686:
1360:
281:
1062:, have better properties for this application.
787:
116:
974:. This yellow solid is one of the most common
760:
1256:Industrial Photoinitiators: A Technical Guide
1329:
1248:
1246:
1026:group adopts a planar, anti-conformation.
350:
241:
219:
1347:
317:
1243:
1145:Other suitable oxidizing agents such as
1336:Journal of the Chilean Chemical Society
1085:Benzil is a standard building block in
346:
1361:
1210:
232:
1252:
483:1.23 g/cm, solid (1.255 g/cm, x-ray)
378:Key: WURBFLDFSFBTLW-UHFFFAOYSA-N
199:
179:
1089:. It condenses with amines to give
388:Key: WURBFLDFSFBTLW-UHFFFAOYAZ
272:
13:
1060:2,2-dimethoxy-2-phenylacetophenone
783:
14:
1385:
900:
656:
441:
47:
38:
29:
1349:10.4067/S0717-97072011000200008
1253:Green, W. Arthur (2010-04-22).
1029:
896:(at 25 °C , 100 kPa).
1323:
1288:
1279:
1226:
1196:
1184:
1172:
1124:
618:Occupational safety and health
447:
435:
1:
1297:Journal of Chemical Education
1166:
1119:tetraphenylcyclopentadienone
1080:
989:
78:1,2-Diphenylethane-1,2-dione
7:
1099:benzilic acid rearrangement
828:or concentration (LD, LC):
10:
1390:
1109:. Benzil also reacts with
473:yellow crystalline powder
414:c1ccccc1C(=O)C(=O)c2ccccc2
409:O=C(C(=O)c1ccccc1)c2ccccc2
15:
966:, generally abbreviated (
890:
850:
846:>3 g/kg (mouse, oral)
824:
637:
615:
610:
574:
422:
397:
362:
100:
84:
72:
60:
55:
46:
37:
28:
1222:10.1002/14356007.a15_077
1129:Benzil is prepared from
703:Precautionary statements
87:Diphenylethane-1,2-dione
16:Not to be confused with
1022:derivatives), the (RCO)
978:. Its main use is as a
564:Magnetic susceptibility
1153:) are used routinely.
794:
1193:A60 (8-9) 1805 (2004)
1058:derivatives, such as
1042:networks. It absorbs
793:
74:Systematic IUPAC name
1093:ligands. A classic
776:(fire diamond)
62:Preferred IUPAC name
1309:1988JChEd..65..553D
1238:10.1021/j100290a017
1133:, for example with
1111:1,3-diphenylacetone
1065:Benzil is a potent
510:Solubility in water
465: g·mol
161:Beilstein Reference
66:Diphenylethanedione
25:
1157:Iron(III) chloride
1135:copper(II) acetate
1115:aldol condensation
1006:of 117°. In less
996:carbon-carbon bond
948:with the formula (
923:Infobox references
851:Related compounds
795:
23:
1317:10.1021/ed065p553
1191:Spectrochim. Acta
1179:Acta Crystallogr.
1097:of benzil is the
1087:organic synthesis
1071:carboxylesterases
984:polymer chemistry
931:Chemical compound
929:
928:
872:Related compounds
681:Hazard statements
582:Crystal structure
570:-118.6·10 cm/mol
331:CompTox Dashboard
149:Interactive image
142:Interactive image
1381:
1369:Aromatic ketones
1354:
1353:
1351:
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1095:organic reaction
946:organic compound
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430:Chemical formula
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918: ?)
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110:
96:
95:Diphenylglyoxal
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68:
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21:
12:
11:
5:
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1377:
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1265:
1259:. p. 31.
1242:
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1183:
1181:B43 398 (1987)
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1126:
1123:
1082:
1079:
1052:photobleaching
1031:
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1023:
1004:dihedral angle
991:
988:
980:photoinitiator
971:
963:
955:
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899:
898:
894:standard state
891:
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733:P305+P351+P338
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1103:benzilic acid
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598:Dipole moment
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569:
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560:
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554:
550:
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539:diethyl ether
536:
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499:Boiling point
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489:Melting point
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348:DTXSID3044380
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233:ECHA InfoCard
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1270:. Retrieved
1255:
1228:
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1174:
1155:
1144:
1128:
1084:
1064:
1033:
1030:Applications
993:
938:
934:
933:
877:benzophenone
825:
772:
672:
639:
627:Main hazards
616:
294:RTECS number
201:ChEMBL189886
101:Identifiers
85:Other names
1147:nitric acid
1125:Preparation
1048:cross-links
1044:ultraviolet
1020:oxalic acid
1010:analogues (
840:median dose
826:Lethal dose
667:Signal word
621:(OHS/OSH):
470:Appearance
423:Properties
239:100.004.689
181:CHEBI:51507
1363:Categories
1342:(2): 663.
1303:(6): 553.
1272:2022-05-21
1167:References
1091:diketimine
651:Pictograms
575:Structure
549:Solubility
535:Solubility
521:Solubility
515:insoluble
458:Molar mass
319:S85X61172J
212:ChemSpider
129:3D model (
108:CAS Number
1374:Diketones
1107:phenytoin
1081:Reactions
1069:of human
1067:inhibitor
990:Structure
976:diketones
859:diketones
757:P403+P233
749:P337+P313
745:P332+P313
729:P304+P340
725:P302+P352
642:labelling
301:DD1925000
260:205-157-0
252:EC Number
93:Bibenzoyl
91:Dibenzoyl
1204:"Benzil"
1117:to give
1016:biacetyl
1008:hindered
998:of 1.54
885:bibenzil
865:diacetyl
857:Related
773:NFPA 704
632:Irritant
611:Hazards
566:(χ)
557:soluble
543:soluble
529:soluble
118:134-81-6
1305:Bibcode
1131:benzoin
1075:enzymes
1040:polymer
1012:glyoxal
916:what is
914: (
881:glyoxal
673:Warning
553:benzene
525:ethanol
479:Density
463:210.232
270:PubChem
166:608047
24:Benzil
1263:
1113:in an
1056:Acetal
1036:curing
937:(i.e.
935:Benzil
911:verify
908:
402:SMILES
192:ChEMBL
89:Benzil
56:Names
18:benzyl
1159:(FeCl
367:InChI
172:ChEBI
131:JSmol
1261:ISBN
1149:(HNO
765:P501
761:P405
753:P362
741:P321
737:P312
721:P280
717:P271
713:P264
709:P261
695:H335
691:H319
687:H315
603:3.8
310:UNII
283:8651
221:8329
1344:doi
1313:doi
1234:doi
1218:doi
1038:of
982:in
970:CO)
640:GHS
591:21
589:1,2
551:in
537:in
523:in
336:EPA
273:CID
1365::
1340:56
1338:.
1334:.
1311:.
1301:65
1299:.
1245:^
1137::
1121:.
1073:,
1018:,
1014:,
986:.
968:Ph
960:CO
939:Bz
836:50
834:LD
763:,
759:,
755:,
751:,
747:,
743:,
739:,
735:,
731:,
727:,
723:,
719:,
715:,
711:,
693:,
689:,
644::
587:P3
445:10
439:14
1352:.
1346::
1319:.
1315::
1307::
1275:.
1240:.
1236::
1220::
1206:.
1161:3
1151:3
1024:2
1000:Å
972:2
964:2
962:)
956:5
954:H
952:6
950:C
941:2
906:Y
842:)
838:(
814:0
807:1
800:2
605:D
451:2
448:O
442:H
436:C
338:)
334:(
133:)
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
