Mandelonitrile

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Mandelonitrile[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-hydroxy-2-phenylacetonitrile
Other names
α-hydroxybenzeneacetonitrile
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.758
KEGG
Properties
C8H7NO
Molar mass 133.15 g mol−1
Density 1.117 g/mL at 25 °C
Melting point −10 °C (14 °F; 263 K) dl-Form[3]
Boiling point 170 °C (338 °F; 443 K) decomposes[2]
Hazards
Main hazards toxic
R-phrases R23/24/25 R36/37/38 R41
S-phrases 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).
YesY verify (what is YesYN ?)
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.[4]

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:[5]

Preparation of mandelonitrile.png

References[edit]

  1. ^ Sigma-Aldrich product page
  2. ^ The Merck Index, 12th edition, 1996.
  3. ^ The Merck Index, 12th edition, 1996.
  4. ^ Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK , (1992), 279
  5. ^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Org. Synth.  ; Coll. Vol., 1, p. 336