40:
323:
204:
919:
31:
530:
941:
520:
525:
751:
831:-chlorobenzoic acid (10%) and water. The peroxyacid can be purified by washing the commercial material with a sodium hydroxide and potassium phosphate solution buffered at pH = 7.5. Peroxyacids are generally slightly less acidic than their carboxylic acid counterparts, so the acid impurity can be extracted if the
538:
500:
812:. mCPBA is often preferred to other peroxy acids because of its relative ease of handling. mCPBA is a strong oxidizing agent that may cause fire upon contact with flammable material.
963:(LUMO), corresponding, in arrow-pushing terms, to formation of one C-O bond and cleavage of the O-O bond and formation of the other C-O bond and cleavage of the C=C π bond.
652:
644:
937:
geometry of the alkene starting material is retained in the epoxide ring of the product. The transition state of the
Prilezhaev reaction is given below:
764:
947:
The geometry of the transition state, with the peracid bisecting the C-C double bond, allows the two primary frontier orbital interactions to occur: π
835:
is carefully controlled. The purified material is reasonably stable against decomposition if stored at low temperatures in a plastic container.
372:
759:
648:
1130:
1099:
580:
161:
982:
1120:
1074:
337:
771:
1016:
481:
1125:
871:
926:
827:
It is sold commercially as a shelf-stable mixture that is less than 72% mCPBA, with the balance made up of
574:
270:
199:
39:
301:
632:
529:
457:
859:
672:
211:
628:
692:
318:
519:
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801:
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512:
676:
668:
279:
181:
58:
660:
636:
8:
137:
127:
322:
203:
886:
733:
608:
999:
Rao, A. Somasekar; Mohan, H. Rama; Charette, André (2005). "m‐Chloroperbenzoic Acid".
584:
1095:
1070:
1038:
1012:
918:
875:
821:
809:
729:
820:
mCPBA can be prepared by reacting m-chlorobenzoyl chloride with a basic solution of
1047:
1004:
656:
395:
1008:
243:
838:
In reactions where the exact amount of mCPBA must be controlled, a sample can be
704:
596:
30:
742:
696:
616:
612:
1114:
1051:
624:
447:
192:
940:
1032:
McDonald, Richard N.; Steppel, Richard N. & Dorsey, James E. (1970). "
688:
910:
906:
708:
664:
640:
592:
426:
212:
172:
959:(HOMO, regarded as a filled p orbital on a sp hybridized oxygen) to π*
684:
1094:(2nd ed.). Berlin, Heidelberg, New York: Springer. p. 323.
894:
562:
290:
741:
Except where otherwise noted, data are given for materials in their
452:
92 to 94 °C (198 to 201 °F; 365 to 367 K) decomposes
839:
712:
160:
898:
890:
882:
867:
863:
805:
620:
230:
1064:
851:
566:
902:
879:
855:
680:
254:
150:
1092:
Name
Reactions: A Collection of Detailed Reaction Mechanisms
1069:(4th ed.). Oxford: Butterworth-Heinemann. p. 145.
588:
306:
604:
558:
832:
1031:
356:
InChI=1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
346:
InChI=1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
842:to determine the exact amount of active oxidant.
1112:
998:
909:. The following scheme shows the epoxidation of
242:
815:
136:
1001:Encyclopedia of Reagents for Organic Synthesis
804:. It is a white solid often used widely as an
700:
939:
850:The main areas of use are the conversion of
1065:Armarego, W. L. F.; Perrin, D. D. (1996).
321:
202:
180:
278:
977:
975:
317:
1113:
1083:
994:
992:
193:
972:
349:Key: NHQDETIJWKXCTC-UHFFFAOYSA-N
1067:Purification of Laboratory Chemicals
63:3-Chlorobenzene-1-carboperoxoic acid
989:
359:Key: FQAWBGAIOYWONH-UHFFFAOYAN
233:
13:
1089:
38:
29:
14:
1142:
917:
749:
528:
523:
518:
495:Oxidizing, corrosive, explosive
413:
407:
745:(at 25 °C , 100 kPa).
1131:Reagents for organic chemistry
1058:
1025:
482:Occupational safety and health
416:
401:
1:
1009:10.1002/047084289X.rc140.pub2
966:
824:, followed by acidification.
983:"3-Chloroperoxybenzoic acid"
845:
816:Preparation and purification
7:
985:. Organic Chemistry Portal.
25:
10:
1147:
83:3-Chlorobenzoperoxoic acid
77:3-Chloroperoxybenzoic acid
20:-Chloroperoxybenzoic acid
1036:-Chloroperbenzoic Acid".
860:Baeyer-Villiger oxidation
787:-Chloroperoxybenzoic acid
739:
718:
499:
479:
474:
388:
368:
333:
120:
95:-Chloroperoxybenzoic acid
89:-Chloroperoxybenzoic acid
69:
57:
52:
24:
1121:3-Chlorophenyl compounds
1052:10.15227/orgsyn.050.0015
575:Precautionary statements
80:3-Chloroperbenzoic acid
944:
380:ClC1=CC(C(OO)=O)=CC=C1
101:-Chloroperbenzoic acid
43:
34:
1090:Li, Jie Jack (2003).
943:
927:epoxidation mechanism
802:peroxycarboxylic acid
42:
33:
1126:Organic peroxy acids
59:Preferred IUPAC name
901:, and oxidation of
872:Prilezhaev reaction
434: g·mol
21:
945:
929:is concerted: the
887:Rubottom oxidation
772:Infobox references
734:peroxybenzoic acid
719:Related compounds
44:
35:
16:
1101:978-3-662-05338-6
1039:Organic Syntheses
883:α-hydroxy ketones
876:silyl enol ethers
874:), conversion of
822:hydrogen peroxide
810:organic synthesis
780:Chemical compound
778:
777:
730:peroxyacetic acid
725:Related compounds
553:Hazard statements
302:CompTox Dashboard
162:Interactive image
48:
47:
1138:
1106:
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1087:
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1080:
1062:
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1023:
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996:
987:
986:
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889:), oxidation of
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396:Chemical formula
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15:
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769:
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767: ?)
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65:
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12:
11:
5:
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770:
748:
747:
743:standard state
740:
737:
736:
727:
724:
721:
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715:
653:P305+P351+P338
645:P303+P361+P353
637:P301+P330+P331
578:
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1119:
1118:
1116:
1103:
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1078:
1076:0-7506-3761-7
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1045:
1041:
1040:
1035:
1028:
1020:
1014:
1010:
1006:
1002:
995:
993:
984:
978:
976:
971:
964:
942:
938:
936:
932:
928:
920:
916:
915:
914:
912:
908:
904:
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869:
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836:
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738:
735:
731:
728:
723:
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579:
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571:
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543:
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536:
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531:
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503:
498:
494:
489:
488:
484:
483:
478:
473:
469:
463:
459:
456:
455:
451:
449:
448:Melting point
446:
445:
442:White powder
441:
438:
437:
430:
428:
425:
424:
400:
397:
393:
392:
387:
378:
377:
374:
367:
353:
343:
342:
339:
332:
324:
320:
319:DTXSID0061325
316:
315:
313:
303:
299:
298:
294:
292:
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274:
272:
269:
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261:
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210:
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194:ECHA InfoCard
191:
190:
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171:
170:
163:
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60:
56:
51:
41:
37:
32:
28:
27:
23:
19:
1091:
1085:
1066:
1060:
1043:
1037:
1033:
1027:
1000:
955:(LUMO) and n
951:(HOMO) to σ*
946:
934:
930:
924:
913:with mCPBA.
907:amine oxides
849:
837:
828:
826:
819:
795:
794:
790:
784:
783:
782:
544:
501:
491:Main hazards
480:
461:
255:RTECS number
121:Identifiers
107:
98:
92:
86:
70:Other names
17:
911:cyclohexene
905:to produce
864:epoxidation
539:Signal word
485:(OHS/OSH):
439:Appearance
389:Properties
200:100.012.111
1115:Categories
1018:0471936235
967:References
895:sulfoxides
513:Pictograms
427:Molar mass
280:G203D4H1RB
173:ChemSpider
149:3D model (
128:CAS Number
846:Reactions
697:P403+P235
693:P403+P233
689:P370+P378
677:P337+P313
673:P333+P313
669:P332+P313
649:P304+P340
641:P302+P352
504:labelling
291:UN number
262:SD9470000
221:213-322-3
213:EC Number
899:sulfones
891:sulfides
840:titrated
475:Hazards
138:937-14-4
868:alkenes
852:ketones
806:oxidant
800:) is a
765:what is
763: (
458:Acidity
231:PubChem
1098:
1073:
1046:: 15.
1015:
903:amines
856:esters
760:verify
757:
545:Danger
432:172.56
373:SMILES
53:Names
935:trans
880:silyl
791:mCPBA
470:7.57
338:InChI
295:3106
244:70297
182:63480
151:JSmol
110:-CPBA
104:mCPBA
1096:ISBN
1071:ISBN
1013:ISBN
925:The
897:and
798:CPBA
785:meta
713:P501
709:P420
705:P411
701:P405
685:P363
681:P362
665:P321
661:P312
657:P310
633:P280
629:P272
625:P271
621:P264
617:P261
613:P260
609:P243
605:P242
601:P241
597:P240
593:P234
589:P233
585:P220
581:P210
567:H335
563:H314
559:H226
271:UNII
99:meta
87:meta
18:meta
1048:doi
1005:doi
961:C=C
953:O-O
949:C=C
933:or
931:cis
893:to
878:to
866:of
862:),
854:to
808:in
793:or
502:GHS
307:EPA
234:CID
1117::
1044:50
1042:.
1011:.
1003:.
991:^
974:^
833:pH
732:;
711:,
707:,
703:,
699:,
695:,
691:,
687:,
683:,
679:,
675:,
671:,
667:,
663:,
659:,
655:,
651:,
647:,
643:,
639:,
635:,
631:,
627:,
623:,
619:,
615:,
611:,
607:,
603:,
599:,
595:,
591:,
587:,
583:,
565:,
561:,
506::
467:)
460:(p
414:Cl
1104:.
1079:.
1055:.
1050::
1034:m
1021:.
1007::
957:O
885:(
870:(
858:(
829:m
796:m
789:(
755:N
465:a
462:K
420:3
417:O
411:5
408:H
405:7
402:C
309:)
305:(
153:)
108:m
93:m
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