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1,3 Propanedithiol

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Density  1.08 g/cm³
Appearance  Colorless liquid
1,3-Propanedithiol httpsuploadwikimediaorgwikipediacommonsthu
Related compounds  1,2-ethanedithiol 1,2-propanedithiol lipoic acid

1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.

Contents

Use in organic synthesis

1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. The reactivity of this dithiane illustrates the concept of umpolung.

The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.

1,3-Propanedithiol is used in the synthesis of tiapamil.

Use in inorganic synthesis

1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:

Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO

Safety

The stench of 1,3-propanedithiol can be neutralized with bleach.

References

1,3-Propanedithiol Wikipedia


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