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| Propanoic anhydride | |
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| IUPAC name | Propanoyl propanoate |
| Other names | Propionic anhydride |
| Identifiers | |
| CAS number | [123-62-6] |
| RTECS number | UF9100000 |
| Properties | |
| Molecular formula | 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 |
| Solubility in water | Reacts to give propionic acid |
| Viscosity | 1.144 cP at ?°C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | flammable |
| R-phrases | R34 |
| S-phrases | S26-45 |
| Flash point | 63 °C |
| 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 |
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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.
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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
- ^ Williams, J. W. Krynitsky, J. A. (1955). "n-Caproic Anhydride". Org. Synth.; Coll. Vol. 3.
- ^ Drugs of Abuse Publication, Chapter 2
