(chloromethylidene)dimethylazanium chloride

• ChemBase编号: 148986
• 分子式: C3H7Cl2N
• 平均质量: 128.00038
• 单一同位素质量: 126.99555459
• SMILES: C[N+](=CCl)C.[Cl-]
• Canonical SMILES: ClC=[N+](C)C.[Cl-]
• InChI: InChI=1S/C3H7ClN.ClH/c1-5(2)3-4;/h3H,1-2H3;1H/q+1;/p-1
• InChIKey: QQVDYSUDFZZPSU-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: (chloromethylidene)dimethylazanium chloride
• IUPAC传统名: (chloromethylidene)dimethylazanium chloride
• 别名: 氯甲叉二甲基氯化铵; 维尔斯梅尔试剂; (氯亚甲基)二甲基氯化铵; Arnold′s reagent; Dimethylchloroformiminium chloride; (Chlormethylene)dimethylammonium chloride; Vilsmeier reagent; (Chloromethylene)dimethyliminium chloride; Arnold's Reagent; N,N-Dimethylchloroformimidinium chloride; (Chloromethylene)dimethylammonium chloride

登记号

• CAS号: 3724-43-4
• EC号: 425-970-6
• MDL号: MFCD00011868
• Beilstein号: 3566322
• PubChem SID: 24855124; 162243156; 24856957
• PubChem CID: 77311

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): -3.0188434
• LogD (pH = 7.4): -3.0188434
• Log P: -3.0188434
• 摩尔折射率: 35.0771 cm^3
• 极化性: 9.141899 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: 130°C dec.; 132 °C (dec.)(lit.)

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 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: 61-14-22-35
• 安全公开号: 53-26-36/37/39-45; 53-45
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS06; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H360-H314-H318; H302-H314-H360D
• GHS警示性声明: P201-P280-P305 + P351 + P338-P310; P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• 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 P2 (EN 143) respirator cartridges, type P3 (EN 143) respirator cartridges; 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
• 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: ≥97.0% (AT); 95%; 96%
• 级别: purum
• 杂质: <5% DMF
• 线性分子式: ClCH=N(CH3)2Cl

详细说明

Sigma Aldrich - 280909

Application
用 β-氨基酸通过羧基活化与环化脱水作用来制备 β-内酰胺的试剂。9也用于将 α-氨基腈转化为 4-氯咪唑。10
Reagent or Reactant for the synthesis of:
• β-Lactams vis the Staudinger reaction1
• N-vinyl substituted indoles via cross coupling of NH-indoles with vinyl bromides2
• Multi ring-fused 2-pyridone-based fluorescent scaffold3
• ester prodrugs as anti-poxvirus agents4
• Trimethine cyanine dyes for sensing G-quadruplex formation5
• Phospha-isosteres via Hundsdiecker-Barton iododecacarboxylation6
• 2-Azetidinones via [2+2]-cycloaddition7Used for studying organic photosensitizers for application in dye-sensitized solar cells8
包装
5, 25 g in glass bottle

Sigma Aldrich - 25130

Other Notes
制备杂环化合物9的试剂；用于芳香烃的甲酰化10
Application
Reagent or Reactant for the synthesis of:
• β-Lactams vis the Staudinger reaction1
• N-vinyl substituted indoles via cross coupling of NH-indoles with vinyl bromides2
• Multi ring-fused 2-pyridone-based fluorescent scaffold3
• ester prodrugs as anti-poxvirus agents4
• Trimethine cyanine dyes for sensing G-quadruplex formation5
• Phospha-isosteres via Hundsdiecker-Barton iododecacarboxylation6
• 2-Azetidinones via [2+2]-cycloaddition7Used for studying organic photosensitizers for application in dye-sensitized solar cells8

参考文献

• Preformed, crystalline Vilsmeier reagent useful in, e.g. formylation, dehydration, and chlorination reactions, avoiding the use of POCl₃, COCl₂, (COCl)₂, etc. For further information on Vilsmeier reagents, see N,N-Dimethylformamide, A13547. Review: Adv. Org. Chem., 9, 225 (1976). Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994).
• Reacts with alcohols to form iminium salts which undergo nucleophilic displacement under mild conditions with inversion of configuration. The advantages of this approach over the equivalent Mitsunobu reactions (see Triphenylphosphine, L02502) for the activation of alcohols towards nucleophiles are that it is more suitable for scale-up and that the by-products are easily separated and of low mass. For use in cyclodehydration of hydroxy phenols in the synthesis of ɑ ₂-adrenoreceptor antagonists, see: Tetrahedron Lett., 34, 7483 (1993):
  
• Similarly, iminium salts of secondary alcohols undergo nucleophilic displacement with K benzoate giving the ester of opposite configuration in high yield and ee: J. Chem. Soc., Chem. Commun., 1403 (1995).