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T30805

Sigma-Aldrich

Thioacetic acid

96%

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Synonym(s):
TAA, TMA, Thiacetic acid
Linear Formula:
CH3COSH
CAS Number:
Molecular Weight:
76.12
Beilstein/REAXYS Number:
1733298
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
241776163678172502
Thioacetic acid 96%

T30805

Thioacetic acid

Potassium thioacetate 98%

241776

Potassium thioacetate

Thioacetamide ACS reagent, ≥99.0%

163678

Thioacetamide

Thioacetamide reagent grade, 98%

172502

Thioacetamide

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

bp

88-91.5 °C (lit.)

bp

-

bp

-

bp

-

refractive index

n20/D 1.465 (lit.)

refractive index

-

refractive index

-

refractive index

-

density

1.065 g/mL at 25 °C (lit.)

density

-

density

-

density

-

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

flash_point_c

18 °C

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)
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)
Organocatalytic enantioselective Michael addition of thioacetic acid to enones.
Li Hao, et al.
Tetrahedron Letters, 47(18), 3145-3148 (2006)
Md Ashraful Hoque et al.
Bioorganic & medicinal chemistry letters, 22(21), 6770-6772 (2012-10-02)
Two thioacetate tails were introduced to the chlamydocin- and CHAP31-related cyclic tetrapeptides. An intramolecular disulfide bridge could be formed in the CHAP31-related cyclic peptides. Both the thioacetate-tailed and disulfide-bridged peptides were potent histone deacetylase inhibitors in the presence of sulfhydryl
Brian C Smith et al.
Biochemistry, 46(50), 14478-14486 (2007-11-22)
Sir2 protein deacetylases (or sirtuins) catalyze NAD+-dependent conversion of epsilon-amino-acetylated lysine residues to deacetylated lysine, nicotinamide, and 2'-O-acetyl-ADP-ribose. Small-molecule modulation of sirtuin activity might treat age-associated diseases, such as type II diabetes, obesity, and neurodegenerative disorders. Here, we have evaluated

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