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Thioacetamide

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Thioacetamide
Structural formula
Ball-and-stick model
Names
IUPAC name Thioacetamide
Preferred IUPAC name Ethanethioamide
Other names acetothioamide, TAA, thioacetimidic acid, TA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.493 Edit this at Wikidata
KEGG
PubChem CID
RTECS number
  • AC8925000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)Key: YUKQRDCYNOVPGJ-UHFFFAOYSA-N
  • 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 colourless crystals, slight mercaptan odor
Density 1.269 g/cm³
Melting point 115 °C
Boiling point decomp.
Solubility in water good, with hydrolysis
Structure
Crystal structure monoclinic
Hazards
Occupational safety and health (OHS/OSH):
Main hazards stench
Flash point ?°C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Coordination chemistry

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:

M + CH3C(S)NH2 + H2O → MS + CH3C(O)NH2 + 2 H (M = Ni, Pb, Cd, Hg)

Related precipitations occur for sources of soft trivalent cations (As, Sb, Bi) and monovalent cations (Ag, Cu).

Preparation

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

CH3C(O)NH2 + 1/4 P4S10 → CH3C(S)NH2 + 1/4 P4S6O4

Structure

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.

Safety

Thioacetamide is carcinogen class 2B. It is known to produce marked hepatotoxicity in exposed animals. This is evidenced by enzymatic changes, which include elevation in the levels of serum alanine transaminase, aspartate transaminase and aspartic acid.

References

  1. George Schwarz (1955). "2,4-Dimethylthiazole". Organic Syntheses; Collected Volumes, vol. 3, p. 332.
  2. Mary R. Truter "An accurate determination of the crystal structure of thioacetamide" Journal of the Chemical Society, 1960, pp. 997-1007. DOI: 10.1039/JR9600000997
  3. http://www.sciencedirect.com/science/article/pii/S0378874199001531
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