Thioacetamide

Thioacetamide

Names
IUPAC name Thioacetamide
Preferred IUPAC name Ethanethioamide
Other names acetothioamide, TAA, thioacetimidic acid, TA, TAM
Identifiers
CAS Number	62-55-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:32497 Y
ChemSpider	2006126 Y
ECHA InfoCard	100.000.493
KEGG	C19302 N
PubChem CID	2723949
RTECS number	AC8925000
UNII	075T165X8M Y
InChI InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) Y Key: YUKQRDCYNOVPGJ-UHFFFAOYSA-N Y InChI=1/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) Key: YUKQRDCYNOVPGJ-UHFFFAOYAD
SMILES S=C(N)C
Properties
Chemical formula	C2H5NS
Molar mass	75.13 g/mol
Appearance	cristalls colourless crystals
Odor	slight mercaptan
Density	1.269 g/cm3
Melting point	115 °C (239 °F; 388 K)
Boiling point	decomposes
Solubility in water	good
Magnetic susceptibility (χ)	-42.45·10−6 cm3/mol
Structure
Crystal structure	monoclinic
Hazards
Main hazards	Foul stench, carcinogenic
Safety data sheet	MSDS
R-phrases (outdated)	R22, R36, R37, R45
S-phrases (outdated)	S45, S53
Related compounds
Related compounds	acetamide, dithioacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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:

Related precipitations occur for sources of soft trivalent cations (As³⁺, Sb³⁺, Bi³⁺) and monovalent cations (Ag⁺, Cu⁺).

Thioacetamide is prepared by treating acetamide with phosphorus pentasulfide as shown in the following idealized reaction:

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.