Tetramethylthiuram Monosulfide

image [97‐74‐5] C 6 H 12 N 2 S 3 (MW 208.367) InChI = 1S/C6H12N2S3/c1‐7(2)5(9)11‐6(10)8(3)4/h1‐4H3 InChIKey = REQPQFUJGGOFQL‐UHFFFAOYSA‐N (reagent used as a sulfur transfer agent, source of monosulfide for carbon(sp 2 )‐sulfur bond formation or thioacylation) Alternative Names: monothiuram, tetramethyl thiuram monosulfide, tetramethylthiodicarbonic diamide, dimethylcarbamothioyl N , N ‐dimethylcarbamodithioate, TMTM. Physical Data: mp 106–110 °C, d 1.37 g cm −3 . Solubility: insoluble in H 2 O; soluble in most organic solvents such as EtOH, acetone, benzene, and diethyl ether. Form Supplied in: yellow powder, widely available. Preparative Methods: coupling from dithiocarbamic acid salt and dimethylcarbamothioic chloride. 1 Purification: can be purified by chromatography column, R f (50% ethyl acetate in hexane) 0.40. 1 Handling, Storage, and Precautions: the product is stable under standard ambient conditions. Present acute toxicity and aquatic hazard. Careful use due to odor. Forms explosive mixtures with air upon intense heating and decomposes to NO x , CO 2 , CO, or sulfur oxides. Incompatible with strong oxidizers. The reactivity and uses can be compared to thiram (also named tetramethylthiuram disulfide [137‐26‐8]).