Mandelonitrile

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Mandelonitrile[1]
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 532-28-5 YesY
PubChem 10758
ChemSpider 10304 YesY
KEGG C00561 YesY
ChEBI CHEBI:16910 YesY
Jmol-3D images Image 1
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 (235 °F; 386 K)
Related compounds
Related compounds mandelic acid, phenylacetonitrile
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.

Occurrence[edit]

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[edit]

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]

Preparation of mandelonitrile.png

References[edit]

  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. ; Coll. Vol. 1: 336