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Key Documents

T30805

Sigma-Aldrich

Thioacetic acid

96%

Synonym(s):

TAA, TMA, Thiacetic acid

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About This Item

Linear Formula:
CH3COSH
CAS Number:
Molecular Weight:
76.12
Beilstein:
1733298
EC Number:
MDL number:
UNSPSC Code:
12352106
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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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.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

64.4 °F - closed cup

Flash Point(C)

18 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
M Eguchi et al.
Medical electron microscopy : official journal of the Clinical Electron Microscopy Society of Japan, 34(1), 61-70 (2001-08-02)
Cytochemical and ultrastructural studies of 42 patients with acute nonlymphoblastic leukemia (ANLL) lacking myeloperoxidase as detected by light microscopy were performed. These ANLL patients were classified into minimally differentiated acute myeloid leukemia (AML-M0) (26 cases), mixed-lineage leukemia (9 cases), and
Wen Yang et al.
Organic & biomolecular chemistry, 10(34), 6876-6884 (2012-08-01)
A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent

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