Tert-Butylthiol
chemical compound
tert-Butylthiol, also known as tert-butyl mercaptan (TBM), and abbreviated t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol has a strong odor. It is considered a flavoring agent.
Preparation
tert-Butylthiol was first prepared in 1890 by Leonard Dobbin by the reaction of zinc sulfide and t-butyl chloride.
The compound was later prepared by the reaction of the Grignard reagent, t-BuMgCl, with sulfur to give the corresponding thiolate, followed by hydrolysis. This preparation is shown below:
t-BuMgCl + S → t-BuSMgCl
t-BuSMgCl + H2O → t-BuSH + Mg(OH)Cl
It is made industrially by the reaction of isobutylene with hydrogen sulfide over a clay (silica alumina) catalyst.
Reactions
tert-Butylthiol is deprotonated by lithium hydride in an aprotic solvent such as hexamethylphosphoramide (HMPA). The resulting lithium thiolate salt has been used as demethylating reagent. For example, treatment with 7-methylguanosine gives guanosine. Other N-methylated nucleosides in tRNA are not demethylated by this reagent.
tert-Butylthiol reacts with thallium(I) ethoxide to give the thallium thiolate:
(CH3)3CSH + CH3CH2O−Tl+ → (CH3)3CS−Tl+ + CH3CH2OH
This thallium thiolate can be used to convert acyl chlorides to the thioester:
(CH3)3CS−Tl+ + RCOCl → RCOSC(CH3)3 + TlCl
(CH3)3CSLi reacts with MoCl4 with to give the tetrathiolate complex:
MoCl4 + 4 (CH3)3CSLi → ((CH3)3CS)4Mo + 4 LiCl
Commercial use and occurrence
tert-Butylthiol is the main ingredient in many gas odorant blends.
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