Potassium thioacetate is an
organosulfur compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
and a
salt
In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
with the formula . This white, water-soluble solid is used as a
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
for preparing thioacetate
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s and other derivatives.
Synthesis and reactions
Potassium thioacetate, which is commercially available, can be prepared by combining
acetyl chloride
Acetyl chloride () is an acyl chloride derived from acetic acid (). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.
Synthesis
On an ...
and
potassium hydrogen sulfide:
:
It arises also by the neutralization of
thioacetic acid
Thioacetic acid is an organosulfur compound with the molecular formula . It is a thioic acid: the sulfur Structural analog, analogue of acetic acid (), as implied by the ''thio-'' prefix. It is a yellow liquid with a strong thiol-like odor. It is ...
with
potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash.
Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which utili ...
.
Use in preparation of thiols
In a common application, potassium thioacetate is combined with
alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...
s to give
thioacetate esters (X =
halide
In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fl ...
):
:
Hydrolysis of these esters affords
thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...
s:
:
The thioacetate esters can also be cleaved with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of pent-4-yne-1-thiol:
:
:{{chem2, H3C(CH2)3SAc + HSMe -> H3C(CH2)3SH + MeSAc
References
Reagents for organic chemistry
Organosulfur compounds
Potassium compounds