Cyclopropylacetylene is an hydrocarbon with the chemical formula . Under normal conditions, the substance is a colorless liquid. Cyclopropylacetylene is a precursor pharmaceuticals and other organic compounds.

Synthesis

Several methods have been published on the synthesis of cyclopropylacetylene. The earliest preparation starts with the chlorination of cyclopropylmethylketone with phosphorus pentachloride. Thereafter, the reaction product, 1-cyclopropyl-1,1-dichloroethane, is converted into cyclopropylacetylene via double dehydrochlorination. This occurs in presence of a strongly basic solution, such as potassium ''tert''-butoxide in

dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds a ...

However, the yield of this method is not substantial (20-25%). A one-pot synthesis of cyclopropylacetylene has been reported in which 5-chloro-1-pentyne reacts with ''n''-butyl lithium or ''n''-hexyl lithium.

Cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

is used as a solvent. The reaction is a metalation followed by a cyclization. The reaction product is then cooled, and an aqueous solution of ammonium chloride is added slowly. There is a two-phase mixture: a heavy water phase and a lighter organic phase containing cyclopropylacetylene. Cyclopropylacetyleen synthese 2

Applications

Cyclopropylacetylene is used as reagent in organic reactions. It is, for example, a building block of the

antiretroviral The management of HIV/AIDS normally includes the use of multiple antiretroviral drugs as a strategy to control HIV infection. There are several classes of antiretroviral agents that act on different stages of the HIV life-cycle. The use of multipl ...

and psychotropic drug

efavirenz Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlest ...

. It can also be used in the azide-alkyne Huisgen cycloaddition.

References

{{Reflist Ethynyl compounds Cyclopropyl compounds