| Pin | Propanoyl chloride |
|---|---|
| Othernames | Propionic chloride; propionic acid chloride (1:1) |
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.
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.[globalize]
Synthesis
Propionyl chloride is industrially produced by chlorination of propionic acid with phosgene:[4]
- CH3CH2CO2H + COCl2 → CH3CH2COCl + HCl + CO2
References
- ^ Michael B Smith (22 November 2016). Organic Synthesis. Elsevier Science. p. 165. ISBN 978-0-12-800807-2.
- ^ 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
- ^ "Propionyl Chloride". 12 October 2023.
- ^