N,N-Dimethylthioformamide

Abstract

[758-16-7] C3H7NS (MW 89.18) InChI = 1S/C3H7NS/c1-4(2)3-5/h3H,1-2H3 InChIKey = SKECXRFZFFAANN-UHFFFAOYSA-N (Vilsmeier reagent for formylation of aliphatic, aromatic, and heteroaromatic systems; acyl anion equivalent; thiolysis of alkyl, aryl, and acyl halides; conversion of oximes into nitriles; reduction of sulfoxides; formation of some sulfur heterocycles and formamidines) Alternate Name: TDMF. Physical Data: bp 58–60 °C/1 mmHg; d 1.047 g cm−3; nD20 1.5760; fp 99 °C. Solubility: sol THF, ethyl acetate, toluene, DMF; may react with some halogenated solvents. Form Supplied in: yellow to colorless liquid. Analysis of Reagent Purity: characterized by 1H and 13C NMR spectroscopy.2 Preparative Methods: various methods have been reported3 for the preparation of TDMF. As with other thioamides, it is best obtained by treatment of the parent amide with a suitable thionating reagent (see also 2,4‐Bis(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane 2,4‐Disulfide) (eq 1).3d More recently, efficient conversion has been effected using Phosphorus(V) sulfide that has been activated using solid Sodium Carbonate (eq 2).3a (1) (2) Purification: distillation under reduced pressure. Handling, Storage, and Precautions:can be stored for long periods of time at rt if kept sealed under inert atmosphere and out of direct contact with light; use in a fume hood.