Propionyl chloride

Propionyl 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.

Propionyl chloride
Names
IUPAC name
Propanoyl chloride
Other names
Propionic chloride
Identifiers
3D model (JSmol)
ECHA InfoCard 100.001.064
UNII
Properties
C3H5ClO
Molar mass 92.52 g·mol−1
Appearance colorless liquid
Density 1.0646 g/cm3
Melting point −94 °C (−137 °F; 179 K)
Boiling point 80 °C (176 °F; 353 K)
Hazards
Flash point 54 °C (129 °F; 327 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

Synthesis

Propionyl chloride is industrially produced by chlorination of propionic acid with phosgene:[3]

CH3CH2CO2H + COCl2 → CH3CH2COCl + HCl + CO2

References

  1. Michael B Smith (22 November 2016). Organic Synthesis. Elsevier Science. p. 165. ISBN 978-0-12-800807-2.
  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. 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.
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