N-氯代丁二酰亚胺

N-氯代丁二酰亚胺[1]
IUPAC名
1-chloropyrrolidine-2,5-dione
英文名 N-Chlorosuccinimide
别名 N-氯代琥珀酰亚胺
缩写 NCS
识别
缩写 NCS
CAS号 128-09-6  checkY
PubChem 31398
ChemSpider 29129
SMILES
 
  • O=C1N(Cl)C(=O)CC1
InChI
 
  • 1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
InChIKey JRNVZBWKYDBUCA-UHFFFAOYAN
EINECS 204-878-8
性质
化学式 C4H4ClNO2
摩尔质量 133.53 g·mol−1
外观 白色单斜结晶
密度 1.65 g/cm3
熔点 148-150 °C(421-423 K)
溶解性 14 g/L (20°C)
危险性
欧盟危险性符号
腐蚀性腐蚀性 C
警示术语 R:R22, R34
安全术语 S:S26, S36/37/39 S45
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

N-氯代丁二酰亚胺(NCS)是丁二酰亚胺N-氯代衍生物

性质

白色单斜晶体,有的气味。稍溶于氯仿四氯化碳

制取

丁二酸氨化得到丁二酰亚胺,再在乙酸水溶液中用次氯酸钠在低温下发生氯化,并经离心、洗涤、干燥得成品。[2]

用途

有机合成中的氯化剂[3]和温和氧化剂[4]。它是Corey-Kim氧化反应中的试剂。

参见

参考资料

  1. ^ [1] at Sigma-Aldrich
  2. ^ N-氯代丁二酰亚胺. 化工引擎. [2009-09-24]. (原始内容存档于2008-12-11). 
  3. ^ Delaney, Paul A.; R. Johnstone. Solvent effects in the chlorination of tetrahydrothiophens with N-chlorosuccinimide. Tetrahedron. 1985, 41 (18): 3845–3851. doi:10.1016/S0040-4020(01)91405-X. 
  4. ^ Kim, Kwan Soo; I. Cho, B. Yoo, Y. Song and C. Hahn. Selective oxidation of primary and secondary alcohols using di-isopropyl sulphide–N-chlorosuccinimide. J. Chem. Soc., Chem. Commun. 1984: 762–763. doi:10.1039/C39840000762. 

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