Propionyl chloride

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Propionyl chloride
Propanoyl chloride skeletal.svg
Names
Preferred IUPAC name
Propanoyl chloride
Other names
Propionic chloride; propionic acid chloride (1:1)
Identifiers
3D model (JSmol)
ECHA InfoCard 100.001.064 Edit this at Wikidata
UNII
  • CCC(=O)Cl
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
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive, flammable; highly toxic
Flash point 54 °C (129 °F; 327 K)
Lethal dose or concentration (LD, LC):
100 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Synthesis[edit]

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

CH3CH2CO2H + COCl2 → CH3CH2COCl + HCl + CO2

References[edit]

  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.