(Chloromethylene)dimethylammonium chloride

• Catalog No.: B24172
• CAS Number: 3724-43-4
• M. F.: C3H7Cl2N
• M. W.: 128.00038
• Purity: 96%

SYNONYMS

• Title: (氯亚甲基)二甲基氯化铵
• IUPAC name: (chloromethylidene)dimethylazanium chloride
• IUPAC Traditional name: (chloromethylidene)dimethylazanium chloride
• Synonyms: N,N-Dimethylchloroformimidinium chloride; Arnold's Reagent

DATABASE IDS

• Beilstein Number: 3566322
• MDL Number: MFCD00011868
• CAS Number: 3724-43-4
• EC Number: 425-970-6

PROPERTIES

• Purity: 96%
• Melting Point: 130°C dec.
• GHS Hazard statements: H301-H360-H314-H318
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 61-14-22-35
• Safety Statements: 53-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II

REFERENCES

• 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).