Thioformamide
Title: Thioformamide
CAS Registry Number: 115-08-2
CAS Name: Methanethioamide
Molecular Formula: CH3NS
Molecular Weight: 61.11
Percent Composition: C 19.65%, H 4.95%, N 22.92%, S 52.47%
Line Formula: HCSNH2
Literature References: Prepd by the action of phosphorus pentasulfide on formamide: Willstätter, Wirth, Ber. 42, 1911 (1909). Synthesis: Erlenmeyer, Menzi, Helv. Chim. Acta 31, 2071 (1948); Schmitz, US 2682558 (1954 to du Pont); R. Tull, L. M. Weinstock, Angew. Chem. Int. Ed. 8, 278 (1969). Spectroscopic studies: R. Sugisaki et al., J. Mol. Spectrosc. 49, 241 (1974); R. H. Judge et al., Can. J. Chem. 65, 2100 (1987). Use in synthesis of thiazoles: T. J. Cousineau, J. A. Secrist III, J. Org. Chem. 44, 4351 (1979); H. Fukatsu et al., Heterocycles 29, 1517 (1989).
Properties: Prisms from ethyl acetate or from ether + petr ether, mp 26-27°. uv max (CH3OH): 263 nm (e 12500). Turns yellow and dec to a dark-colored mass. May be stored as soln in abs ether, preferably over P2O5. Sol in water (with considerable cooling). Freely sol in tetrahydrofuran, alcohol, ether, acetone, ethyl acetate; sparingly sol in cold chloroform, benzene, petr ether, carbon disulfide. The decompn products are hydrogen cyanide, hydrogen sulfide, ammonia, and some solid, amorphous, sulfur-contg compounds.
Melting point: mp 26-27°
Absorption maximum: uv max (CH3OH): 263 nm (e 12500)
 
Derivative Type: Monohydrate
Properties: Yellow oil.
 
Use: In the synthesis of the thiazole containing compds.

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