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(Chloromethylene)dimethylammonium chloride, 96%, Thermo Scientific ChemicalsHave Questions?
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Catalog number B24172.14
also known as B24172-14
Price (USD)/ Each
147.00
-
Quantity:
25 g
Price (USD)/ Each
147.00
(Chloromethylene)dimethylammonium chloride, 96%, Thermo Scientific Chemicals
Catalog numberB24172.14
Price (USD)/ Each
147.00
-
Chemical Identifiers
CAS3724-43-4
IUPAC Namechloro(dimethylamino)methylium chloride
Molecular FormulaC3H7Cl2N
InChI KeyQQVDYSUDFZZPSU-UHFFFAOYSA-M
SMILES[Cl-].CN(C)[CH+]Cl
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Specifications
Specification Sheet
Specification SheetFormCrystals or powder or crystalline powder
Appearance (Color)White to yellow
Assay (Titration ex Chloride)≥95.0 to ≤105.0%
(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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
(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.
Solubility
Soluble in water.
Notes
Moisture sensitive. It may decompose in moist air/ water. Incompatible with bases, strong oxidizing agents, amines, metals and butyl rubber.
(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.
Solubility
Soluble in water.
Notes
Moisture sensitive. It may decompose in moist air/ water. Incompatible with bases, strong oxidizing agents, amines, metals and butyl rubber.
RUO – Research Use Only
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).
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.
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).
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.