Propionyl chloride

Propionyl chloride
Names
Preferred IUPAC name
Propanoyl chloride
Other names
Propionic chloride; propionic acid chloride (1:1)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.064
EC Number
  • 201-170-0
UNII
UN number 1815 (PROPIONYL CHLORIDE)
  • InChI=1S/C3H5ClO/c1-2-3(4)5/h2H2,1H3
    Key: RZWZRACFZGVKFM-UHFFFAOYSA-N
  • 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)
1.404
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive, flammable; highly toxic
GHS labelling:[1]
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
3
2
W
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).
Infobox references

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

  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. ^ "Propionyl Chloride". 12 October 2023.
  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 978-3-527-30673-2.
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