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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]
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.
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).
The conjugate base of thioacetic acid, thioacetate, is a reagent used for installing thiol groups via the displacement of alkyl halides by a two-step process. The halide is displaced to give a thioester intermediate, which is then hydrolyzed: R−X + CH 3 COS − → R−SC(O)CH 3 + X −
A related two-step process involves alkylation of thiosulfate to give the thiosulfonate ("Bunte salt"), followed by hydrolysis. The method is illustrated by one synthesis of thioglycolic acid: ClCH 2 CO 2 H + Na 2 S 2 O 3 → Na[O 3 S 2 CH 2 CO 2 H] + NaCl Na[O 3 S 2 CH 2 CO 2 H] + H 2 O → HSCH 2 CO 2 H + NaHSO 4
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]
It arises also by the neutralization of thioacetic acid with potassium hydroxide. Use in preparation of thiols. In a common application, ...
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 ...