Molar mass 133.15 g/mol Density 1.12 g/cm³ | Formula C8H7NO Boiling point 170 °C | |
 | ||
Related compounds | ||
Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.
Contents
Occurrence
Mandelonitrile is the aglycone part of the cyanogenic glycosides prunasin and amygdalin.
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.
Mandelonitrile is broken down into cyanide and benzaldehyde by the enzyme mandelonitrile lyase.
Preparation
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:
