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{{DISPLAYTITLE:''N''-Chlorosuccinimide}} |
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{{DISPLAYTITLE:''N''-Chlorosuccinimide}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Name=''N''-Chlorosuccinimide |
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| Name=''N''-Chlorosuccinimide |
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| verifiedrevid = 444019639 |
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| verifiedrevid = 444020789 |
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| Reference = <ref> at ]</ref> |
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| Reference = <ref> at ]</ref> |
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| ImageFileL1 = N-Chlorosuccinimide.svg |
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| ImageFileL1 = 1-chloropyrrolidine-2,5-dione 200.svg |
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| ImageSizeL1 = 120px |
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| ImageSizeL1 = 130 |
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| ImageAltL1 = Skeletal formula of ''N''-chlorosuccinimide |
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| ImageFileR1 = N-Chlorosuccinimide-3D.png |
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| ImageFileR1 = N-Chlorosuccinimide-3D.png |
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| ImageAltR1 = Space-filling model of the ''N''-chlorosuccinimide molecule |
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| ImageSzieR1 = 120px |
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| IUPACName = 1-chloropyrrolidine-2,5-dione |
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| PIN = 1-Chloropyrrolidine-2,5-dione |
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| OtherNames = Chlorosuccinimide |
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| OtherNames = Chlorosuccinimide |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = NCS |
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| Abbreviations = NCS |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 128-09-6 |
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| CASNo = 128-09-6 |
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| EINECS = 204-878-8 |
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| EINECS = 204-878-8 |
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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 = 0FWP306H7X |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| SMILES = C1CC(=O)N(C1=O)Cl |
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| ChemSpiderID = 29129 |
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| InChI = InChI=1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 |
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| ChEBI = 53203 |
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| ChEMBL = 2107513 |
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| Gmelin = 122816 |
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| Beilstein = 113915 |
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| SMILES = O=C1N(Cl)C(=O)CC1 |
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| InChI = 1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 |
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| InChIKey = JRNVZBWKYDBUCA-UHFFFAOYAN |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JRNVZBWKYDBUCA-UHFFFAOYSA-N |
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}} |
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}} |
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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=4|H=4|Cl=1|N=1|O=2 |
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| MolarMass = |
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| MolarMass = |
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| Appearance = Solid |
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| Appearance = white solid |
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| MeltingPtCL = 148 |
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| MeltingPtC = 148 to 150 |
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| Density = 1.65 g/cm<sup>3</sup> |
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| MeltingPtCH = 150 |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS05}}{{GHS07}} |
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| EUClass = Corrosive ('''C''') |
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| GHSSignalWord = Danger |
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| RPhrases = {{R22}} {{R34}} |
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| HPhrases = {{H-phrases|302|314|319|335|412}} |
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| SPhrases = {{S26}} {{S36/37/39}} {{S45}} |
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| PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+312|301+330+331|303+361+353|304+340|305+351+338|310|312|321|330|337+313|363|403+233|405|501}} |
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}} |
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}} |
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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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| OtherFunctn = ] </BR>] |
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| OtherFunction = ] <br>]<br>] |
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'''''N''-Chlorosuccinimide''' ('''NCS''') is the ] with the formula C<sub>2</sub>H<sub>4</sub>(CO)<sub>2</sub>NCl. This white solid is used for chlorinations.<ref name=sym>{{cite journal|title=Applications of ''N''-chlorosuccinimide in organic synthesis |
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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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|last1=Golebiewski|first1=W. Marek|last2=Gucma|first2=Miro slaw|journal=Synthesis |year=2007|issue=23 |pages=3599–3619|doi= 10.1055/s-2007-990871}}</ref> It is also used as a mild ].<ref>{{cite journal |last=Kim|first=Kwan Soo |author2=I. Cho |author3=B. Yoo |author4=Y. Song |author5=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> NCS is related to succinimide, but with N-Cl in place of N-H. The N–Cl bond is highly reactive, and NCS functions as a source of "Cl<sup>+</sup>". |
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==Synthesis and selected reactions== |
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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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NCS is produced from ] by treatment with {{chem2|Cl+}} sources, such as ] (bleach), and ], and even ].<ref name=sym/> |
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Electron-rich arenes are readily monochlorinated by NCS. ] and ] are converted to the respective chlorinated derivatives.<ref name=sym/> |
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==Related reagents== |
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* ] (NIS), the ] analog of ''N''-chlorosuccinimide.<ref>{{cite journal |last=Beebe |first=T. R. |author2=R. L. Adkins |author3=C. C. Bogardus |author4=B. Champney |author5=P. S. Hii |author6=P. Reinking |author7=J. Shadday |author8=W. D. Weatherford |author9=M. W. Webb |author10=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> |
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* ] (NBS), the ] analog of ''N''-chlorosuccinimide.<ref>{{cite journal |last=Castanet |first=Anne-Sophie |author2=F. Colobert |author3=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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* Other ''N''-chloro compounds that are commercially available include ], ] ((OCNCl)<sub>3</sub>), 1,3-dichloro-5,5-dimethylhydantoin.<ref name=sym/> |
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==Further reading== |
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* {{cite journal |last=Delaney |first=Paul A. |author2=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 }} |
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* ''N''-chlorosuccinimide has been employed as chlorinating agent in combination with visible-light photoredox catalysts in organic synthesis.<ref>{{Cite journal |last1=Rogers |first1=David A. |last2=Gallegos |first2=Jillian M. |last3=Hopkins |first3=Megan D. |last4=Lignieres |first4=Austin A. |last5=Pitzel |first5=Amy K. |last6=Lamar |first6=Angus A. |date=2019-09-06 |title=Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes |url=https://www.sciencedirect.com/science/article/pii/S0040402019308257 |journal=Tetrahedron |volume=75 |issue=36 |pages=130498 |doi=10.1016/j.tet.2019.130498 |issn=0040-4020|url-access=subscription}}</ref> |
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== References == |
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== References == |
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==External links== |
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==External links== |
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* and at |
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* and at |
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{{DEFAULTSORT:Chlorosuccinimide, N-}} |
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{{DEFAULTSORT:Chlorosuccinimide, N-}} |
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