9977. Viehe's Salt

Nomenclature

CAS number: 33842-02-3
N-(Dichloromethylene)-N-methylmethanaminium chloride; N-(dichloromethylene)-N,N-dimethyliminium chloride; N,N-dimethylphosgeniminium chloride; phosgeniminium chloride.
C3H6Cl3N; mol wt 162.45.
C 22.18%, H 3.72%, Cl 65.47%, N 8.62%.

Description and references

Electrophilic chlorinating reagent. Prepn: H. G. Viehe, Z. Janousek, Angew. Chem. 83, 614 (1971); and chemistry: eidem, Angew. Chem. Int. Ed. 12, 806 (1973). 35Cl NMR study: G. Jugie et al., J. Chem. Soc. Perkin Trans. 2 1975, 925. Review of chemistry: Z. Janousek, H. G. Viehe, J. Prakt. Chem. Chem.-Ztg. 336, 561-562 (1994); of applications in synthesis of heterocyclic compounds: J. M. Quintela et al., Recent Res. Dev. Org. Chem. 2, 409-418 (1998).

Chemical structure

Properties

Colorless, hygroscopic solid, fp ≈180°.

Use

Chlorinating agent; introduces amide chloride groups into activated substrates. Building block in organic synthesis.