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Propionyl chloride

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Propionyl chloride
Names
Preferred IUPAC name Propanoyl chloride
Other names Propionic chloride; propionic acid chloride (1:1)
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.001.064 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CCC(=O)Cl
Properties
Chemical formula C3H5ClO
Molar mass 92.52 g·mol
Appearance colorless liquid
Density 1.0646 g/cm
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):
LD50 (median dose) 100 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
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. 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.

There have been efforts 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:

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. https://www.federalregister.gov/documents/2023/10/12/2023-22570/propionyl-chloride
  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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