Pyrrolidine: Properties and Uses

Pyrrolidine is an organic compound also known as azolidine, tetrahydropyrrole, azacyclopentane, and prolamine. The molecular formula of the chemical is (CH2)4NH. Pyrrolidine CAS number is 123-75-1.

The substance is a cyclic secondary amine that is classified as a saturated heterocycle. Pyrrolidine ring structure widely occurs in natural and synthetic chemistry. It is present in natural alkaloids (e.g. hygrine, nicotine), in drugs (bepridil, procyclidine). The chemical serves as the basis for the racetam compounds, like piracetam, aniracetam, etc. Such amino acids like proline and hydroxyproline are also considered as the derivatives of this organic.

General Properties

Pyrrolidine is a colorless to pale yellow liquid with an unpleasant characteristic odor, usually described as ammoniacal, shellfish-, and seaweed-like. It is also characterized by the following properties:

  • Molar mass: 71.12 g·mol-1;
  • Density: 0.866 g/cm3;
  • Melting point: -63 °C;
  • Boiling point: 87 °C.

The chemical is miscible with water, soluble in ethanol, ethyl ether, and only slightly soluble in chloroform and benzene. Its liquid and vapor are highly flammable. The flash point of the substance is 3 °C; autoignition temperature is 345 °C.

Pyrrolidine is a base, with its basicity resembling other dialkyl amines. However, it is remarkable for its compactness, a consequence of its cyclic structure.

Synthesis and Uses

This organic is made by treatment of 1,4-butanediol with ammonia over an oxide catalyst. Among the multiple pyrrolidine uses, its application as a building block in the synthesis of complex organic compounds is believed to be the most important. It is used in the synthesis of N-benzoyl pyrrolidine from benzaldehyde. This chemical serves as a catalyst in the process of N-sulfinyl aldimines synthesis from sulfonamides and carbonyl compounds. It is also applied for the activation of aldehydes and ketones.

In food industry, this substance if often applied as a flavoring agent. In pharmaceutical industry, it is appreciated for the anti-inflammatory and hepatoprotective properties. 

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