(Dichloromethylene)dimethylammonium chloride

• Catalog No.: A12300
• CAS Number: 33842-02-3
• M. F.: C3H6Cl3N
• M. W.: 162.44544
• Purity: 95%

SYNONYMS

• Title: (二氯亚甲基)二甲基氯化铵
• IUPAC name: (dichloromethylidene)dimethylazanium chloride
• IUPAC Traditional name: (dichloromethylidene)dimethylazanium chloride
• Synonyms: N,N-Dimethylphosgeniminium chloride; "Phosgeniminium chloride"

DATABASE IDS

• CAS Number: 33842-02-3
• EC Number: 251-695-4
• MDL Number: MFCD00011870
• Beilstein Number: 4157987

PROPERTIES

• Risk Statements: 14-34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Purity: 95%
• Melting Point: ca 185°C dec.

REFERENCES

• 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).