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771:
The preparation of tosyl esters and amides are conducted in the presence of a base, which absorbs hydrogen chloride. The selection of the base is often crucial to the efficiency of tosylation. Typical bases include
504:
1066:
436:
780:. Unusual bases are also used; for example, catalytic amounts of trimethylammonium chloride in the presence of triethylamine is highly effective by virtue of the
291:
1105:
458:
936:
792:
Being a widely available reagent, TsCl has been heavily examined from the perspective of reactivity. It is used in dehydrations to make
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765:
220:
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This reagent is inexpensively available for laboratory use. It is a by-product from the production of
611:(abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"):
56:
608:
237:
90:
969:
804:. In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH
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1004:
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Cyclization of 1,1-Difluoro-1-alkenes: Synthesis of 3-Butyl-2-Fluoro-1-Tosylindole"
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991:
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470:
702:
Thus, tosylation followed by reduction allows for removal of a hydroxyl group.
797:
337:
135:
1075:
837:
1064:
Lindner, O.; Rodefeld, L. "Benzenesulfonic Acids and Their
Derivatives".
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416:
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832:-toluenesulfonyl chloride (a precursor for the synthesis of the common
801:
793:
578:
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175:
761:
are non-basic and, when derived from primary amines, are even acidic.
481:
Except where otherwise noted, data are given for materials in their
935:
Whitaker, D. T.; Whitaker, K. S.; Johnson, C. R.; Haas, J. (2006).
602:
123:
113:
225:
654:
Tosylates can be cleaved with lithium aluminium hydride:
428:
360:
65 to 69 °C (149 to 156 °F; 338 to 342 K)
499:
265:
InChI=1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
275:
InChI=1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
990:
Ichikawa, J.; Nadano, R.; Mori, T.; Wada, Y. (2006).
370:134 °C (273 °F; 407 K) at 10 mmHg
187:
432:
99:
1067:Ullmann's Encyclopedia of Industrial Chemistry
948:Encyclopedia of Reagents for Organic Synthesis
915:"P-TOLUENESULFONYL CHLORIDE (TOSYL CHLORIDE)"
8:
240:
165:
143:
26:
1031:Whitmore, F. C.; Hamilton, F. H. (1922).
207:
607:In characteristic manner, TsCl converts
930:
928:
926:
924:
906:
561:Cl. This white, malodorous solid is a
296:
261:
236:
475:128 °C (262 °F; 401 K)
156:
268:Key: YYROPELSRYBVMQ-UHFFFAOYSA-N
7:
764:TsCl reacts with hydrazine to give
278:Key: YYROPELSRYBVMQ-UHFFFAOYAN
178:
61:4-Methylbenzene-1-sulfonyl chloride
705:Likewise, TsCl is used to prepare
25:
840:), via the chlorosulfonation of
489:
42:
33:
893:Tosyl chloride is "a corrosive
485:(at 25 °C , 100 kPa).
1106:Reagents for organic chemistry
394:Occupational safety and health
1:
956:10.1002/047084289X.rt136.pub2
937:"P-Toluenesulfonyl Chloride"
1019:, vol. 11, p. 834
766:p-toluenesulfonyl hydrazide
74:-toluenesulfonyl chloride,
28:4-Toluenesulfonyl chloride
1137:
1052:, vol. 1, p. 492
600:
524:4-Toluenesulfonyl chloride
342:190.65 g/mol
18:4-toluenesulfonyl chloride
1033:"Sodium Toluenesulfinate"
944:-Toluenesulfonyl Chloride
531:-toluenesulfonyl chloride
479:
391:
386:
307:
287:
252:
83:
67:
55:
50:
41:
32:
1076:10.1002/14356007.a03_507
950:. New York: John Wiley.
577:, it is a derivative of
1121:Foul-smelling chemicals
1070:. Weinheim: Wiley-VCH.
439:
411:on contact with water
299:O=S(Cl)(=O)c1ccc(cc1)C
438:
421:(fire diamond)
57:Preferred IUPAC name
545:with the formula CH
377:Solubility in water
29:
539:-sulfonyl chloride
512:Infobox references
440:
382:Reacts with water
27:
1116:P-Tosyl compounds
1050:Collected Volumes
1038:Organic Syntheses
1017:Collected Volumes
1005:Organic Syntheses
631:Cl + ROH → CH
567:organic synthesis
520:Chemical compound
518:
517:
221:CompTox Dashboard
125:Interactive image
16:(Redirected from
1128:
1111:Sulfonyl halides
1090:
1089:
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968:. Archived from
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591:functional group
543:organic compound
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315:Chemical formula
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70:Tosyl chloride,
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788:Other reactions
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581:and contains a
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565:widely used in
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757:The resulting
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601:Main article:
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483:standard state
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972:on 2016-03-05
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836:and catalyst
835:
834:food additive
831:
823:
821:
803:
799:
795:
787:
785:
783:
779:
778:triethylamine
775:
769:
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712:
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709:from amines:
708:
703:
657:
656:
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650:
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596:
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592:
585:chloride (−SO
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366:Boiling point
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356:Melting point
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157:ECHA InfoCard
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985:
974:. Retrieved
970:the original
947:
943:
940:
909:
892:
827:
791:
770:
763:
759:sulfonamides
756:
707:sulfonamides
704:
701:
674:OR + LiAlH
653:
606:
574:
570:
536:
534:
528:
527:
523:
522:
417:
403:Main hazards
392:
350:White solid
84:Identifiers
75:
71:
68:Other names
895:lachrymator
824:Manufacture
798:isocyanides
733:NH → CH
471:Flash point
397:(OHS/OSH):
347:Appearance
308:Properties
163:100.002.441
78:-TsCl, TsCl
1100:Categories
976:2013-05-28
901:References
884:Cl + HCl
338:Molar mass
209:027KYN78B4
136:ChemSpider
112:3D model (
91:CAS Number
838:saccharin
678:→ LiAl(O
407:Releases
802:diimides
794:nitriles
774:pyridine
729:Cl + R
609:alcohols
583:sulfonyl
541:) is an
535:toluene-
418:NFPA 704
387:Hazards
332:S
889:Hazards
842:toluene
647:OR +
579:toluene
563:reagent
505:what is
503: (
176:PubChem
101:98-59-9
1082:
962:
753:+ HCl
698:+ 4 RH
500:verify
497:
292:SMILES
51:Names
1012:: 111
868:→ CH
860:+ SO
830:ortho
603:Tosyl
575:TosCl
257:InChI
114:JSmol
1080:ISBN
1045:: 89
998:trig
994:endo
960:ISBN
820:Na.
800:and
776:and
658:4 CH
597:Uses
589:Cl)
571:TsCl
200:UNII
189:7397
145:7119
1072:doi
992:"5-
952:doi
897:."
649:HCl
573:or
409:HCl
328:ClO
226:EPA
179:CID
1102::
1078:.
1047:;
1041:.
1035:.
1014:;
1010:83
1008:.
1002:.
958:.
946:.
939:.
923:^
880:SO
864:Cl
848:CH
844::
816:SO
796:,
784:.
768:.
749:NR
745:SO
725:SO
713:CH
690:CH
682:SC
670:SO
643:SO
627:SO
615:CH
593:.
557:SO
533:,
1088:.
1074::
1054:.
1043:2
1021:.
996:-
979:.
954::
942:p
917:.
882:2
878:4
876:H
874:6
872:C
870:3
866:2
862:2
858:5
856:H
854:6
852:C
850:3
818:2
814:4
812:H
810:6
808:C
806:3
751:2
747:2
743:4
741:H
739:6
737:C
735:3
731:2
727:2
723:4
721:H
719:6
717:C
715:3
696:4
694:)
692:3
688:4
686:H
684:6
680:3
676:4
672:2
668:4
666:H
664:6
662:C
660:3
645:2
641:4
639:H
637:6
635:C
633:3
629:2
625:4
623:H
621:6
619:C
617:3
587:2
559:2
555:4
553:H
551:6
549:C
547:3
537:p
529:p
526:(
495:N
459:0
452:1
445:3
330:2
326:7
324:H
322:7
320:C
228:)
224:(
116:)
76:p
72:p
20:)
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