Thioacetone
Chemical compound
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Key Takeaways
- Thioacetone is an organosulfur compound belonging to the -thione group called thioketones with a chemical formula (CH 3 ) 2 CS.
- Above −20 °C (−4 °F), thioacetone readily converts to a polymer and a trimer, trithioacetone.
- Thioacetone was first obtained in 1889 by Baumann and Fromm, as a minor impurity in their synthesis of trithioacetone.
- The trimer is prepared by pyrolysis of allyl isopropyl sulfide or by treating acetone with hydrogen sulfide in the presence of a Lewis acid.
Thioacetone is an organosulfur compound belonging to the -thione group called thioketones with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above −20 °C (−4 °F), thioacetone readily converts to a polymer and a trimer, trithioacetone. It has an extremely potent, unpleasant odor, and is considered one of the worst-smelling substances known.
Thioacetone was first obtained in 1889 by Baumann and Fromm, as a minor impurity in their synthesis of trithioacetone.
Preparation
Thioacetone is usually obtained by cracking the cyclic trimer trithioacetone, [(CH3)2CS]3. The trimer is prepared by pyrolysis of allyl isopropyl sulfide or by treating acetone with hydrogen sulfide in the presence of a Lewis acid. The trimer cracks at 500–600 °C (932–1,112 °F) to give the thione.
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