Mandelonitrile

Mandelonitrile[1]
Skeletal formula
Racemic mandelonitrile (ambiguous chirality)
Ball-and-stick model
(S)-Mandelonitrile
Names
IUPAC name
2-Hydroxy-2-phenylacetonitrile
Other names
α-Hydroxybenzeneacetonitrile
Identifiers
3D model (JSmol)
2207122
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.758 Edit this at Wikidata
EC Number
  • 208-532-7
1684586
KEGG
UNII
UN number 2810
  • InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H checkY
    Key: NNICRUQPODTGRU-UHFFFAOYSA-N checkY
  • InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
    Key: NNICRUQPODTGRU-UHFFFAOYAG
  • N#CC(O)c1ccccc1
Properties
C8H7NO
Molar mass 133.150 g·mol−1
Density 1.117 g/mL
Melting point 22 °C (72 °F; 295 K) (R/S)[2]
Boiling point 282.70 °C (540.86 °F; 555.85 K) Decomposes[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
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).
checkY verify (what is checkY☒N ?)

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.

Occurrence

Mandelonitrile is the aglycone part of the cyanogenic glycosides prunasin and amygdalin. Prunasin can be hydrolyzed by the enyzme prunase into glucose and mandelonitrile (for example, when an appleseed is digested in a ruminant's stomach).

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]

References

  1. ^ Sigma-Aldrich product page
  2. ^ a b 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; Collected Volumes, vol. 1, p. 336.