Propionyl chloride
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Names | |
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Preferred IUPAC name Propanoyl chloride | |
Other names Propionic chloride; propionic acid chloride (1:1) | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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ECHA InfoCard | 100.001.064 ![]() |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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Properties | |
Chemical formula | 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): | |
LD50 (median dose) | 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). 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.[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.
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.
- ^ https://www.federalregister.gov/documents/2023/10/12/2023-22570/propionyl-chloride
- ^ 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.