Mandelonitrile

Mandelonitrile[1]
IUPAC name 2-hydroxy-2-phenylacetonitrile
Other names α-hydroxybenzeneacetonitrile
Identifiers
CAS number	532-28-5 Y
PubChem	10758
ChemSpider	10304 Y
KEGG	C00561 Y
ChEBI	CHEBI:16910 Y
Jmol-3D images	Image 1
SMILES N#CC(O)c1ccccc1
InChI InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H Y Key: NNICRUQPODTGRU-UHFFFAOYSA-N Y
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; 235 °F; 386 K
Related compounds
Related compounds	mandelic acid, phenylacetonitrile
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.

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.^[2]

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:^[3]

References