Propionic anhydride

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Propanoic anhydride
Propanoic anhydride.png
Names
Preferred IUPAC name
Propanoic anhydride
Other names
Propionic anhydride
Propanoyl propanoate
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.004.218
RTECS number UF9100000
Properties
C6H10O3
Molar mass 130.14 g/mol
Appearance Clear liquid, with a strong smell similar to vinegar
Density 1.015 g/cm3, liquid
Melting point −42 °C (−44 °F; 231 K)
Boiling point 167 to 170 °C (333 to 338 °F; 440 to 443 K)
Reacts to give propanoic acid
Viscosity 1.144 cP at ?°C
Hazards
Main hazards flammable
Safety data sheet External MSDS
R-phrases R34
S-phrases S26-45
Flash point 63 °C (145 °F; 336 K)
Related compounds
Related compounds
Acetic anhydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Propanoic anhydride is an organic compound with the formula (CH3CH2CO)2O. This simple acid anhydride is a colourless liquid. It is a widely used reagent in organic synthesis.

Synthesis[edit]

Propanoic anhydride has been prepared by dehydration of propanoic acid using ketene:[1]

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

Safety[edit]

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

Legal Status[edit]

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 Administration as a List I chemical under the Controlled Substances Act.[2]

References[edit]

  1. ^ Williams, J. W. Krynitsky, J. A. (1955). "n-Caproic Anhydride". Org. Synth.  ; Coll. Vol., 3 
  2. ^ Drugs of Abuse Publication, Chapter 2