Propionic anhydride
 | |
| Names | |
|---|---|
| IUPAC name
Propanoyl propanoate
| |
| Other names
Propanoic anhydride
| |
| Identifiers | |
| ECHA InfoCard | 100.004.218 |
| RTECS number |
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CompTox Dashboard (EPA)
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| 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 |
| Boiling point | 167–170 °C |
| Reacts to give propanoic acid | |
| Viscosity | 1.144 cP at ?°C |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
|
flammable |
| Flash point | 63 °C (145 °F; 336 K) |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
Propanoic anhydride has been prepared by dehydration of propanoic 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 Administration as a List I chemical under the Controlled Substances Act.[2]
References
- ^ Williams, J. W. Krynitsky, J. A. (1955). "n-Caproic Anhydride". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 3. - ^ Drugs of Abuse Publication, Chapter 2