Propanoic anhydride

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Propanoic anhydride
Propanoic anhydride
General
Systematic name Propanoyl propanoate
Other names Propionic anhydride
Molecular formula C6H10O3
SMILES ?
Molar mass 130.14 g/mol
Appearance Clear liquid, with a strong smell similar to vinegar
CAS number [123-62-6]
Properties
Density and phase 1.015 g/cm³, liquid
Solubility in water Reacts to give propionic acid
Melting point -42 °C
Boiling point 167 - 170 °C
Viscosity 1.144 cP at ?°C
Structure
Dipole moment ? D
Hazards
MSDS External MSDS
Main hazards flammable
NFPA 704
Flash point 63 °C
R/S statement R: R34
S: S26-45
RTECS number UF9100000
Related compounds
Related compounds Acetic anhydride
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Propanoic anhydride, also called propionic anhydride, is a simple acid anhydride. With the chemical formula (CH3CH2CO)2O, it is a widely used reagent in organic synthesis.

Synthesis

Propionic anhydride has been prepared by dehydration of propionic acid using ketene:[1]

2 CH3CH2CO2H + CH2=C=O → (CH3CH2CO)2O + CH3CO2H

Safety

Propanoic anhydride is strong smelling and corrosive, and will cause burns on contact with skin. Vapour can burn eyes and lungs.

Legal Status

Due to its potential use as a precursor in the synthesis of fentanyl and fentanyl analogs, propanoic anhydride is regulated by the United States Drug Enforcement Agency as a List I chemical under the Controlled Substances Act.[2]

References

  1. Williams, J. W. Krynitsky, J. A. “n-Caproic Anhydride” Organic Syntheses, Collected Volume 3, page 164ff (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0164.pdf.
  2. http://www.dea.gov/pubs/abuse/2-chem.htm

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