|Preferred IUPAC name
acetothioamide, TAA, thioacetimidic acid, TA, TAM
|Molar mass||75.13 g/mol|
|Appearance||colourless crystals, slight mercaptan odor|
|Melting point||115 °C (239 °F; 388 K)|
|Main hazards||Foul stench, carcinogenic|
|acetamide, dithioacetic acid|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Thioacetamide is an organosulfur compound with the formula C2H5NS. This white crystalline solid is soluble in water and serves as a source of sulfide ions in the synthesis of organic and inorganic compounds. It is a prototypical thioamide.
Thioacetamide was widely used in classical qualitative inorganic analysis as an in situ source for sulfide ions. Thus, treatment of aqueous solutions of many metal cations to a solution of thioacetamide affords the corresponding metal sulfide:
- M2+ + CH3C(S)NH2 + H2O → MS + CH3C(O)NH2 + 2 H+ (M = Ni, Pb, Cd, Hg)
Related precipitations occur for sources of soft trivalent cations (As3+, Sb3+, Bi3+) and monovalent cations (Ag+, Cu+).
- CH3C(O)NH2 + 1/4 P4S10 → CH3C(S)NH2 + 1/4 P4S6O4
The C2NH2S portion of the molecule is planar; the C-S and C-N distances are 1.713 and 1.324 Å, both indicating multiple bonding.
Thioacetamide is carcinogen class 2B. It is known to produce marked hepatotoxicity in exposed animals. Toxicity values are 301 mg/kg in rats (LD50, oral administration), 300 mg/kg in mice (LD50, intraperitoneal administration). This is evidenced by enzymatic changes, which include elevation in the levels of serum alanine transaminase, aspartate transaminase and aspartic acid.
- Schwarz, G. (1945). "2,4-Dimethylthiazole". Org. Synth. 25: 35.; Coll. Vol. 3, p. 332
- Truter, M. R. (1960). "An accurate determination of the crystal structure of thioacetamide". Journal of the Chemical Society 1960: 997–1007. doi:10.1039/JR9600000997.
- "HSDB: THIOACETAMIDE CASRN: 62-55-5". Hazardous Substances Data Bank.
- Ali, S.; Ansari, K. A.; Jafry, M. A.; Kabeer, H.; Diwakar, G. (2000). "Nardostachys jatamansi protects against liver damage induced by thioacetamide in rats". Journal of Ethnopharmacology 71 (3): 359–363. doi:10.1016/S0378-8741(99)00153-1.
- "Thioacetamide (Sulfo amine)". Chemical Land 21. Retrieved February 14, 2006.