(dichloromethylidene)dimethylazanium chloride

• ChemBase编号: 148068
• 分子式: C3H6Cl3N
• 平均质量: 162.44544
• 单一同位素质量: 160.95658224
• SMILES: C[N+](=C(Cl)Cl)C.[Cl-]
• Canonical SMILES: ClC(=[N+](C)C)Cl.[Cl-]
• InChI: InChI=1S/C3H6Cl2N.ClH/c1-6(2)3(4)5;/h1-2H3;1H/q+1;/p-1
• InChIKey: NRNFKRFWZQQDMD-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: (dichloromethylidene)dimethylazanium chloride
• IUPAC传统名: (dichloromethylidene)dimethylazanium chloride
• 别名: (二氯亚甲基)二甲基氯化铵; Vilsmeier 试剂; 二氯亚甲基二甲基氯化铵; (二氯亚甲基)二甲基氯化铵; Phosgeniminium chloride; (Dichloromethylene)dimethylammonium chloride; Vilsmeier reagent; Dichloromethylene-dimethyliminium chloride; N,N-Dimethylphosgeniminium chloride; "Phosgeniminium chloride"; (Dichloromethylene)dimethylammonium chloride

登记号

• CAS号: 33842-02-3
• EC号: 251-695-4
• MDL号: MFCD00011870
• Beilstein号: 4157987
• PubChem SID: 162242246; 24850009
• PubChem CID: 2723945

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): -1.963418
• LogD (pH = 7.4): -1.963418
• Log P: -1.963418
• 摩尔折射率: 40.2806 cm^3
• 极化性: 11.098925 Å^3
• 极化表面积: 3.01 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

• 熔点: 183-187 °C (dec.)(lit.); ca 185°C dec.

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 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): 3; II
• 危险公开号: 14-34; 14-34-37
• 安全公开号: 26-36/37/39-45
• TSCA收录: 否
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H314-H318; H314-H335
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P280-P305 + P351 + P338-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 3
• 欧盟补充危害声明: Reacts violently with water.
• 保存温度: 2-8°C

产品相关信息

• 纯度: 95%
• 级别: technical grade
• 线性分子式: [Cl2C=N(CH3)2]+Cl-

详细说明

Sigma Aldrich - 162876

Application
向活化底物中引入酰胺氯基团。1
包装
5, 25 g in glass bottle

参考文献

• Reaction with a phenol yields, after hydrolysis, the diaryl carbonate: Angew. Chem. Int. Ed., 10, 573 (1971). For reactions with active methylene compounds, see: Angew. Chem. Int. Ed., 10, 574, 575 (1971). 2-Hydroxy acetophenones lead to 2-dimethylamino chromones: J. Org. Chem., 57, 6502 (1992); 61, 3218 (1996):
  
• Dehydrates aldoximes and aldehyde phenylhydrazones to nitriles: Synthesis, 563 (1974), 201 (1985), respectively. N, N-dialkylureas are dehydrated to carbodiimides: Tetrahedron Lett., 37, 7047 (1996).
• Converts THP protected alcohols directly to alkyl chlorides in good yield: Tetrahedron Lett., 38, 3517 (1997).
• For review of reactions, including use as Mannich or Vilsmeier intermediates, see: Angew. Chem. Int. Ed., 12, 806 (1973).
• See also (Chloromethylene)dimethylammonium chloride, B24172.
• Effects cyanation of electron-rich aromatics and heterocycles: Tetrahedron Lett., 27, 1939 (1986).