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{{DISPLAYTITLE:''N''-Chlorosuccinimide}} |
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{{chembox |
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{{chembox |
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| Name=''N''-Chlorosuccinimide |
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| Name=cyclohexylthiophthalimide |
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| verifiedrevid = 444019639 |
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| verifiedrevid = 444020789 |
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| Reference = |
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| Reference = <ref> at ]</ref> |
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| ImageFile =Cyclohexylthiophthalimid.svg |
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| ImageFileL1 = N-Chlorosuccinimide.svg |
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| ImageSize =200px |
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| ImageSizeL1 = 120px |
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| PIN = 2-(Cyclohexylsulfanyl)-1''H''-isoindole-1,3(2''H'')-dione |
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| ImageFileR1 = N-Chlorosuccinimide-3D.png |
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| OtherNames = |
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| ImageSzieR1 = 120px |
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|Section1={{Chembox Identifiers |
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| IUPACName = 1-chloropyrrolidine-2,5-dione |
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| Abbreviations = CTP |
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| OtherNames = Chlorosuccinimide |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 17796-82-6 |
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| Abbreviations = NCS |
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| EINECS = 2417741 |
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| CASNo_Ref = {{cascite}} |
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| CASNo = 128-09-6 |
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| EINECS = 204-878-8 |
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| PubChem = 31398 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0FWP306H7X |
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| UNII = 50Z9596NJ3 |
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| PubChem = 28777 |
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| SMILES = C1CC(=O)N(C1=O)Cl |
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| ChemSpiderID = 26768 |
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| InChI = InChI=1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 |
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| SMILES = O=C3c1ccccc1C(=O)N3SC2CCCCC2 |
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| InChI = 1/C14H15NO2S/c16-13-11-8-4-5-9-12(11)14(17)15(13)18-10-6-2-1-3-7-10/h4-5,8-10H,1-3,6-7H2 |
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| InChIKey = UEZWYKZHXASYJN-UHFFFAOYAT |
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| StdInChI = 1S/C14H15NO2S/c16-13-11-8-4-5-9-12(11)14(17)15(13)18-10-6-2-1-3-7-10/h4-5,8-10H,1-3,6-7H2 |
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| StdInChIKey = UEZWYKZHXASYJN-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = |C=4|H=4|Cl=1|N=1|O=2 |
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| C=14|H=15|N=1|O=2|S=1 |
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| Appearance = Colourless solid |
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| MolarMass = |
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| Appearance = Solid |
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| MeltingPtC = 90 |
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| MeltingPtCL = 148 |
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| MeltingPtCH = 150 |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| EUClass = Corrosive ('''C''') |
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| RPhrases = {{R22}} {{R34}} |
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| SPhrases = {{S26}} {{S36/37/39}} {{S45}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = <!--]s--> |
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| OtherFunction = |
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| OtherFunctn = ] </BR>] |
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'''Cyclohexylthiophthalimide''' (abbreviated '''CTP''') is an ] that is used in production of ]. It is a white solid, although commercial samples often appear yellow. It features the ] ], being a derivative of ] and ].<ref>Hans-Wilhelm Engels, Herrmann-Josef Weidenhaupt, Manfred Pieroth, Werner Hofmann, Karl-Hans Menting, Thomas Mergenhagen, Ralf Schmoll, Stefan Uhrlandt “Rubber, 4. Chemicals and Additives” in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2004, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a23_365.pub2}}</ref> In the production of ], CTP impedes the onset of ]. |
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'''''N''-Chlorosuccinimide''' is used for chlorinations<ref>{{cite journal |last=Delaney |first=Paul A. |coauthors=R. Johnstone |year=1985 |title=Solvent effects in the chlorination of tetrahydrothiophens with N-chlorosuccinimide |journal=] |volume=41 |issue=18 |pages=3845–3851 |doi=10.1016/S0040-4020(01)91405-X }}</ref> and as a mild ].<ref>{{cite journal |last=Kim|first=Kwan Soo |coauthors=I. Cho, B. Yoo, Y. Song and C. Hahn |year=1984 |title=Selective oxidation of primary and secondary alcohols using di-isopropyl sulphide–N-chlorosuccinimide |journal=] |pages=762–763 |doi=10.1039/C39840000762 |issue=12 }}</ref> |
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''N''-Iodosuccinimide (NIS), the ] analog of ''N''-chlorosuccinimide, and ] (NBS), the ] analog, are used for similar applications.<ref>{{cite journal |last=Beebe |first=T. R. |coauthors=R. L. Adkins, C. C. Bogardus, B. Champney, P. S. Hii, P. Reinking, J. Shadday, W. D. Weatherford, M. W. Webb, and S. W. Yates |year=1983 |title=Primary alcohol oxidation with N-iodosuccinimide |journal=] |pages=3126–3128 |doi=10.1021/jo00166a046 |volume=48 |issue=18 }}</ref><ref>{{cite journal |last=Castanet |first=Anne-Sophie |coauthors=F. Colobert, P. Broutin |year=2002 |title=Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid |journal=]|pages=5047–5048 |doi=10.1016/S0040-4039(02)01010-9 |volume=43 |issue=29 }}</ref> |
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== References == |
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== References == |
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{{reflist}} |
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{{reflist}} |
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==External links== |
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* and at |
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{{DEFAULTSORT:Chlorosuccinimide, N-}} |
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