T30805
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
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-063-8
Beilstein/REAXYS Number:
1733298
MDL number:
Assay:
96%
InChI key
DUYAAUVXQSMXQP-UHFFFAOYSA-N
InChI
1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)
SMILES string
CC(S)=O
assay
96%
Quality Level
bp
88-91.5 °C (lit.)
density
1.065 g/mL at 25 °C (lit.)
storage temp.
2-8°C
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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
hcodes
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
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
Regulatory Information
危险化学品
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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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