1-chloropyrrolidine-2,5-dione

• ChemBase编号: 74324
• 分子式: C4H4ClNO2
• 平均质量: 133.53306
• 单一同位素质量: 132.99305605
• SMILES: N1(C(=O)CCC1=O)Cl
• Canonical SMILES: ClN1C(=O)CCC1=O
• InChI: InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: JRNVZBWKYDBUCA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-chloropyrrolidine-2,5-dione
• IUPAC传统名: chlorosuccinimide
• 别名: N-氯丁二酰亚胺; N-氯代丁二酰亚胺; 1-chloropyrrolidine-2,5-dione; NCS; 1-Chloropyrrolidine-2,5-dione; N-Chlorosuccinimide 99%; N-CHLOROSUCCINIMIDE; Chlorosuccinimide; N-Chlorosuccinimide

登记号

• CAS号: 128-09-6
• EC号: 204-878-8
• MDL号: MFCD00005511
• Beilstein号: 113915
• 默克索引号: 142164
• PubChem SID: 162039243; 24846932
• PubChem CID: 31398
• Chemspider ID: 29129
• 美国药典/FDA物质标识码: 0FWP306H7X
• 维基百科标题: N-Chlorosuccinimide

理论计算性质

• Acid pKa: 18.07768
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.23125698
• LogD (pH = 7.4): -0.23125698
• Log P: -0.23125698
• 摩尔折射率: 27.6177 cm^3
• 极化性: 10.710621 Å^3
• 极化表面积: 37.38 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Solid
• 熔点: 144-148°C; 146-150°C; 148 - 150°C; 148-150 °C; 148-150 °C(lit.)
• 闪点: >110°C
• 密度: 1.65

安全信息

• 保存条件: Room Temperature (15-30°C), Desiccate, Protect from light
• 保存注意事项: Corrosive/Harmful/Light Sensitive/Moisture Sensitive; Moisture Sensitive
• RTECS编号: UY1013500
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); X
• 联合国危险货物编号: 3261; UN3261
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 22-34; R22 R34
• 安全公开号: 26-36/37/39-45; S26 S36/37/39 S45
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H302-H314; H314-H318-H302
• GHS警示性声明: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

产品相关信息

• 纯度: ≥96.0% (RT); 95+%; 98%
• 级别: purum
• Empirical Formula (Hill Notation): C4H4ClNO2

详细说明

MP Biomedicals - 02150658

Crystalline

MP Biomedicals - 05212213

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 109681

Application
区域选择性氯化和氧化剂。
包装
100, 500 g in poly bottle

Sigma Aldrich - 26370

Other Notes
多功能氯化剂和氧化剂；抗菌剂 2；1

参考文献

• Source of positive chlorine in chlorination and oxidation reactions.
• Methyl ketones may be monochlorinated via their Li enolates: J. Org. Chem., 49, 1286 (1984). For the ɑ-chlorination of acid chlorides formed in situ, see: Tetrahedron Lett., 3235 (1974). For chlorination of deactivated anilines, see: Synthesis, 669 (1985).
• In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to alkyl chlorides stereospecifically with inversion: Tetrahedron Lett., 3937 (1973). For a review, see: Org. React., 29, 1 (1983). Amides have been prepared by treatment of a carboxylic acid with NCS/PPh₃ followed by an amine: Synth. Commun., 25,959 (1995).
• With dimethyl sulfide, forms the Corey-Kim reagent, a mild, selective oxidant for alcohols. For a review, see: Synthesis, 857 (1990); for tabulated examples, see: Org. Synth. Coll., 6, 220 (1988).
• Primary alcohols are oxidized cleanly to aldehydes using NCS and a catalytic amount of TEMPO, A12733 under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996).
• NCS in ether is a convenient alternative to hypochlorite for the conversion of amines to N-chloroamines, for use, e.g. in the Hofmann-Loeffler reaction, see: Chem. Ber., 88, 883 (1955).