Mandelonitrile
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Names | |
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IUPAC name
2-hydroxy-2-phenylacetonitrile | |
Other names
α-hydroxybenzeneacetonitrile | |
Identifiers | |
532-28-5 ![]() | |
ChEBI | CHEBI:16910 ![]() |
ChemSpider | 10304 ![]() |
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Jmol-3D images | Image |
KEGG | C00561 ![]() |
PubChem | 10758 |
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Properties | |
C8H7NO | |
Molar mass | 133.15 g mol−1 |
Density | 1.117 g/mL at 25 °C |
Melting point | 28 to 30 °C (82 to 86 °F; 301 to 303 K) |
Boiling point | 17 to 0 °C (63 to 32 °F; 290 to 273 K) |
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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Infobox references | |
Mandelonitrile is a chemical compound of the cyanohydrin class. 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.[2]
Mandelonitrile is broken down into cyanide and benzaldehyde 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:[3]
References
- ↑ Sigma-Aldrich product page
- ↑ Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK , (1992), 279
- ↑ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Org. Synth.; Coll. Vol. 1, p. 336