Mandelonitrile

Mandelonitrile[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-Hydroxy-2-phenylacetonitrile
Other names
α-Hydroxybenzeneacetonitrile
Identifiers
CAS Number
  • 532-28-5 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 2207122
ChEBI
  • CHEBI:16910 checkY
ChEMBL
  • ChEMBL1393845
ChemSpider
  • 10304 checkY
ECHA InfoCard 100.007.758 Edit this at Wikidata
EC Number
  • 208-532-7
Gmelin Reference
 1684586
KEGG
  • C00561 checkY
PubChem CID
  • 10758
UNII
  • 584322E08A checkY
UN number 2810
CompTox Dashboard (EPA)
  • DTXSID2025422 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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).
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Infobox references
Chemical compound

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.

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.