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Thioacetic acid is an organosulfur compound with the molecular formula CH 3 C(O)SH. It is a thioic acid: the sulfur analogue of acetic acid (CH 3 C(O)OH), as implied by the thio-prefix. It is a yellow liquid with a strong thiol-like odor. It is used in organic synthesis for the introduction of thiol groups (−SH) in molecules. [4]
Thioacetic acid; Thiobenzoic acid; Thioformic acid This page was last edited on 23 December 2024, at 17:54 (UTC). Text is available under the Creative Commons ...
In a common application, potassium thioacetate is combined with alkylating agents to give thioacetate esters (X = halide): . CH 3 COSK + RX → CH 3 COSR + KX. Hydrolysis of these esters affords thiols:
At neutral pH, thiocarboxylic acids are fully ionized. Thiocarboxylic acids are about 100 times more acidic than the analogous carboxylic acids. Thiobenzoic acid has a pK a of 2.48 compared with 4.20 for benzoic acid, and thioacetic acid has a pK a near 3.4 compared with 4.72 for acetic acid. [8]
The reaction was first reported in 1949 with thioacetic acid as reagent [3] [4] and rediscovered in 2009. [5] It is used in click chemistry [ 6 ] [ 7 ] [ 8 ] and in polymerization , especially with dendrimers .
Acid anhydrides and some lactones also give thioesters upon treatment with thiols in the presence of a base. Thioesters can be conveniently prepared from alcohols by the Mitsunobu reaction, using thioacetic acid. [6] They also arise via carbonylation of alkynes and alkenes in the presence of thiols. [7]
General structure of a monothioacetal General structure of a dithioacetal. In organosulfur chemistry, thioacetals are the sulfur analogues of acetals (R−CH(−OR) 2).There are two classes: the less-common monothioacetals, with the formula R−CH(−OR')−SR", and the dithioacetals, with the formula R−CH(−SR') 2 (symmetric dithioacetals) or R−CH(−SR')−SR" (asymmetric dithioacetals).
Thioacetamide is known to induce acute or chronic liver disease (fibrosis and cirrhosis) in the experimental animal model. Its administration in rat induces hepatic encephalopathy, metabolic acidosis, increased levels of transaminases, abnormal coagulation, and centrilobular necrosis, which are the main features of the clinical chronic liver disease so thioacetamide can precisely replicate the ...