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T30805

Sigma-Aldrich

Thioacetic acid

96%

Synonym(s):

TAA, TMA, Thiacetic acid

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About This Item

Linear Formula:
CH3COSH
CAS Number:
507-09-5
Molecular Weight:
76.12
Beilstein/REAXYS Number:
1733298
EC Number:
208-063-8
MDL number:
MFCD00004853
UNSPSC Code:
12352106
PubChem Substance ID:
24900104
NACRES:
NA.22

Quality Level

200

assay

96%

refractive index

n20/D 1.465 (lit.)

bp

88-91.5 °C (lit.)

density

1.065 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(S)=O

InChI

1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)

InChI key

DUYAAUVXQSMXQP-UHFFFAOYSA-N

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Application

Thioacetic acid (TAA) can undergo:
  • Enantioselective addition to nitroalkenes to form chiral 1,2-aminothiol derivatives in the presence of a novel sulfinyl urea organocatalyst. This method has been successfully employed in the synthesis of antifungal drug, sulconazole.
  • Asymmetric Michael addition reaction with chalcones in the presence of a bifunctional amine thiourea catalyst to form synthetically useful thioesters.
  • Asymmetric 1,6-conjugate addition with para-quinone methides in the presence of a chiral phosphoric acid catalyst to form chiral sulfur-containing diphenylmethane-type compounds.
  • Conjugate addition to methacrylamides with chiral trans-2,5-disubstituted pyrrolidine auxiliaries to form chiral β-mercaptocarboxylic acid derivatives.

Thioacetic acid is a reagent for introduction of the thiol group into organic molecules.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Eye Dam. 1 - Flam. Liq. 2 - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

64.4 °F - closed cup

flash_point_c

18 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Phosphoric Acid Catalyzed Asymmetric 1, 6?Conjugate Addition of Thioacetic Acid to para?Quinone Methides.
Dong N, et al.
Angewandte Chemie (International Edition in English), 55(4), 1460-1464 (2016)
Organocatalytic enantioselective Michael addition of thioacetic acid to enones.
Li Hao, et al.
Tetrahedron Letters, 47(18), 3145-3148 (2006)
Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries.
Kim B H, et al.
Tetrahedron Asymmetry, 16(6), 1215-1220 (2005)
Christina Wedemeyer-Exl et al.
Organic & biomolecular chemistry, 5(13), 2119-2128 (2007-06-22)
The thiol-dependent methylation of heptamethyl cob(II)yrinate 8r with methyl iodide and methyl tosylate was explored under a variety of conditions. The interaction of the heptamethyl cob(II)yrinate with a variety of thiols was monitored prior to the addition of the methylating
Jianhua Ren
The journal of physical chemistry. A, 110(50), 13405-13411 (2006-12-15)
We studied the effects of polar groups on the gas-phase acidities of carboxylic acids experimentally and computationally. In this connection, the gas-phase acidities (DeltaH(acid), the enthalpy of deprotonation, and DeltaG(acid), the deprotonation free energy) of borane-complexed methylaminoacetic acid ((CH(3))2N(BH(3))CH(2)CO(2)H) and
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