Mandelonitrile

In organic chemistry, mandelonitrile is the nitrile of mandelic acid, or the cyanohydrin derivative of benzaldehyde. Small amounts of mandelonitrile occur in the pits of some fruits.

Mandelonitrile[1]
Names
IUPAC name
2-Hydroxy-2-phenylacetonitrile
Other names
α-Hydroxybenzeneacetonitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.758
KEGG
UNII
Properties
C8H7NO
Molar mass 133.150 g·mol−1
Density 1.117 g/mL
Melting point −10 °C (14 °F; 263 K) (R/S)[2]
Boiling point 170 °C (338 °F; 443 K) Decomposes[2]
Hazards
Main hazards toxic
R-phrases (outdated) R23/24/25 R36/37/38 R41
S-phrases (outdated) S22 S26 S36/37/39 S45
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related compounds
 mandelic acid, phenylacetonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[3]

Mandelonitrile can break down into cyanide and benzaldehyde, a reaction that can be catalyzed 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:[4]

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References
  1. Sigma-Aldrich product page
  2. The Merck Index (12th ed.). 1996.
  3. Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK , (1992), 279
  4. Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 1, p. 336
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