Chemistry:Propionyl chloride
From HandWiki
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| Names | |
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| Preferred IUPAC name
Propanoyl chloride | |
| Other names
Propionic chloride; propionic acid chloride (1:1)
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| EC Number |
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PubChem CID
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| UNII | |
| UN number | 1815 (PROPIONYL CHLORIDE) |
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| 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) |
Refractive index (nD)
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1.404 |
| Hazards | |
| Main hazards | Corrosive, flammable; highly toxic |
| GHS pictograms |  
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| GHS Signal word | Danger |
| H225, H314 | |
| P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P302+361+354Script error: No such module "Preview warning".Category:GHS errors, P303+361+353, P304+340, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P321, P363, P370+378, P403+235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 54 °C (129 °F; 327 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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 | |
Tracking categories (test):
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. https://books.google.com/books?id=bF-dBgAAQBAJ&pg=PA165.
- ↑ 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. https://www.federalregister.gov/documents/2023/10/12/2023-22570/propionyl-chloride.
- ↑ Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223.
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