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T30805

Sigma-Aldrich

Thioacetic acid

96%

Sinonimo/i:

TAA, TMA, Thiacetic acid

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About This Item

Formula condensata:
CH3COSH
Numero CAS:
507-09-5
Peso molecolare:
76.12
Beilstein:
1733298
Numero CE:
208-063-8
Numero MDL:
MFCD00004853
Codice UNSPSC:
12352106
ID PubChem:
24900104
NACRES:
NA.22

Livello qualitativo

200

Saggio

96%

Indice di rifrazione

n20/D 1.465 (lit.)

P. eboll.

88-91.5 °C (lit.)

Densità

1.065 g/mL at 25 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

CC(S)=O

InChI

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

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Applicazioni

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.

Avvertenze

Danger

Indicazioni di pericolo

H225,H301,H317,H318,H332

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

64.4 °F - closed cup

Punto d’infiammabilità (°C)

18 °C - closed cup

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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Sigma-Aldrich

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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)
Krista M Wager et al.
Organic letters, 13(15), 4052-4055 (2011-07-07)
A method for preparing benzyl aryl thioethers utilizing an in situ deprotection of benzyl thioacetates as an alternative to free thiols as starting materials has been developed and optimized. Good to excellent yields of diverse benzyl aryl thioethers are obtained
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
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