Mandelonitrile

Mandelonitrile^[1]

Names
IUPAC name 2-hydroxy-2-phenylacetonitrile
Other names α-hydroxybenzeneacetonitrile
Identifiers
CAS Registry Number	532-28-5 Y
ChEBI	CHEBI:16910 Y
ChemSpider	10304 Y
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 InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H Key: NNICRUQPODTGRU-UHFFFAOYAG
Jmol-3D images	Image
KEGG	C00561 Y
PubChem	10758
SMILES N#CC(O)c1ccccc1
Properties
Chemical formula	C8H7NO
Molar mass	133.15 g mol−1
Density	1.117 g/mL at 25 °C
Melting point	28 to 30 °C (82 to 86 °F; 301 to 303 K)
Boiling point	17 to 0 °C (63 to 32 °F; 290 to 273 K)
Hazards
Main hazards	toxic
R-phrases	R23/24/25 R36/37/38 R41
S-phrases	S22 S26 S36/37/39 S45
Flash point	113 °C (235 °F; 386 K)
Related compounds
Related compounds	mandelic acid, phenylacetonitrile
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 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.

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