| Mandelonitrile[1] | |
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2-hydroxy-2-phenylacetonitrile |
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Other names
α-hydroxybenzeneacetonitrile |
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| Identifiers | |
| CAS number | 532-28-5 |
| PubChem | 10758 |
| ChemSpider | 10304 |
| KEGG | C00561 |
| ChEBI | CHEBI:16910 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H7NO |
| Molar mass | 133.15 g mol−1 |
| Density | 1.117 g/mL at 25 °C |
| Melting point |
28-30 °C |
| Boiling point |
170 °C |
| Hazards | |
| R-phrases | R23/24/25 R36/37/38 R41 |
| S-phrases | S22 S26 S36/37/39 S45 |
| Main hazards | toxic |
| Flash point | 113 °C |
| Related compounds | |
| Related compounds | mandelic acid, phenylacetonitrile |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.
The naturally-occurring (R)-(+) enantiomer finds use as an intermediate in the preparation of optically active α-hydroxy carboxylic acids, α-hydroxy aldehydes, α-hydroxy ketones, and 2-amino alcohols[2].
Mandelonitrile is broken down into cyanide and benzaldehyde by the enzyme mandelonitrile lyase.
Racemic mandelonitrile may be prepared similar to many other cyanohydrins. In a one pot reaction, benzaldehyde is reacted with sodium bisulfite to give the corresponding adduct, which further reacts with aqueous sodium cyanide to give the racemic product:[3]