Thioacetamide

Thioacetamide

Chembox new
Name = Thioacetamide
ImageFile = TA.png ImageName =
IUPACName = Thioacetamide
OtherNames = acetothioamide, ethanethioamide, TAA, thioacetimidic acid, TA
Section1 = Chembox Identifiers
SMILES = CC(N)=S
CASNo = 62-55-5
RTECS = AC8925000
Section2 = Chembox Properties
Formula = C2H5NS
MolarMass = 75.13 g/mol
Appearance = colourless crystals, slight mercaptan odor
Density = 1.269 g/cm³
Solubility = good, with hydrolysis
MeltingPt = 115 °C
BoilingPt = decomp.
Section3 = Chembox Structure
CrystalStruct = monoclinic
Dipole =
Section7 = Chembox Hazards
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/TH/thioacetamide.html MSDS]
MainHazards = stench
FlashPt = ?°C
RPhrases = R22 R36 R37 R45
SPhrases = S45 S53
Section8 = Chembox Related
OtherCpds = acetamide, dithioacetic acid

Thioacetamide is an organosulfur compound with the formula CH3CSNH2. This white crystalline solid is soluble in water and serves as a source of hydrogen sulfide 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::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+).

Preparation

Thioacetamide is prepared by treating acetamide with phosphorus pentasulfide as shown in the following idealized reaction: [OrgSynth | author = George Schwarz | title = 2,4-Dimethylthiazole | collvol = 3 | collvolpages = 332 | year = 1955 | prep = cv3p0332] :CH3C(O)NH2 + 1/4 P4S10 → CH3C(S)NH2 + 1/4 P4S6O4

tructure

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. [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]

afety

Thioacetamide is carcinogen class 2B.

References

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