Propanoyl_chloride

Propionyl chloride

Propionyl chloride

Chemical compound

Propionyl chloride (also propanoyl chloride) is the organic compound with the formula CH3CH2C(O)Cl. It is the acyl chloride derivative of propionic acid. It undergoes the characteristic reactions of acyl chlorides.[1] It is a colorless, corrosive, volatile liquid.

Quick Facts Names, Identifiers ...

It is used as a reagent for organic synthesis. In derived chiral amides and esters, the methylene protons are diastereotopic.[2]

There have been efforts[3] to schedule Propionyl chloride as a DEA List 1 Chemical as it can be used to synthesize fentanyl.

Synthesis

Propionyl chloride is industrially produced by chlorination of propionic acid with phosgene:[4]

CH3CH2CO2H + COCl2 → CH3CH2COCl + HCl + CO2

References

  1. [1]
    Michael B Smith (22 November 2016). Organic Synthesis. Elsevier Science. p. 165. ISBN 978-0-12-800807-2.
  2. [2]
    Gage, James R.; Evans, David A. (1990). "Diastereoselective Aldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2S,3S)-3-Hydroxy-3-phenyl-2-methylpropanoic Acid". Org. Synth. 68: 83. doi:10.15227/orgsyn.068.0083.
  3. [3]
    https://www.federalregister.gov/documents/2023/10/12/2023-22570/propionyl-chloride
  4. [4]
    Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic acid and derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3527306732.
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