Mandelonitrile

Mandelonitrile[1]
IUPAC name 2-hydroxy-2-phenylacetonitrile
Other names α-hydroxybenzeneacetonitrile
Identifiers
CAS number	532-28-5
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 InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H Key: NNICRUQPODTGRU-UHFFFAOYAG
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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

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

1. ^ Sigma-Aldrich product page
2. ^ Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK , (1992), 279
3. ^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941), "Mandelic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0336 ; Coll. Vol. 1: 336