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(Chloromethylene)dimethylammonium chloride is used in the synthesis of beta-lactams, n-vinyl substituted indoles and fused 2-pyridone rings and 2-azetidinones. It is used as a formylating agent and used in the preparation of anti-poxvirus agents. It is used in Staudinger reaction and Hundsdiecker-barton iododecarboxylation reaction. It is widely used for studying organic photosensitizers, which finds application in dye-sensitized solar cells.
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)./n
Carr, J. M.; Tschumper, G. S.; Lathem, A. P. Boyd Group Electronegativity Influence on the Parr Global Electrophilicity of Vilsmeier Reagent-Derived Imidates: New Insights toward Improving Mitsunobu Chemistry. Helv. Chim. Acta 2015, 98 (4), 582-588.
Lu, S. H.; Liu, P. L.; Wong, F. F. Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction. RSC Adv. 2015, 5 (58), 47098-47107.
Hazard Statements: H302-H314-H335-H360D
Harmful if swallowed. Causes severe skin burns and eye damage. May cause respiratory irritation. May damage the unborn child.
Precautionary Statements: P201-P202-P260-P264b-P270-P271-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant