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3724-43-4 - (Chloromethylene)dimethylammonium chloride, 96% - Arnold's Reagent - N,N-Dimethylchloroformimidinium chloride - B24172 - Alfa Aesar

B24172 (Chloromethylene)dimethylammonium chloride, 96%

Numéro de CAS
3724-43-4
Synonymes
Arnold's Reagent
N,N-Dimethylchloroformimidinium chloride

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(Chloromethylene)dimethylammonium chloride, 96%

MDL
MFCD00011868
EINECS
425-970-6

Propriétés chimiques

Formule
C3H7Cl2N
Poids moleculaire
128.00
Point de fusion
130° dec.
Sensibilité
Moisture Sensitive
Solubilité
Soluble in water.

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.

Notes

Moisture sensitive. It may decompose in moist air/ water. Incompatible with bases, strong oxidizing agents, amines, metals and butyl rubber.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H314-H318-H360

Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May damage fertility or the unborn child.

Mentions de prudence: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3566322
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2923.90
TSCA
Yes

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Analytique et matériel de laboratoire