Summary
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.
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| Names | |
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| IUPAC name
2-Hydroxy-2-phenylacetonitrile
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| Other names
α-Hydroxybenzeneacetonitrile
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| Identifiers | |
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3D model (JSmol)
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| 2207122 | |
| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.007.758 |
| EC Number |
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| 1684586 | |
| KEGG |
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PubChem CID
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| UNII |
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| UN number | 2810 |
CompTox Dashboard (EPA)
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| 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
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toxic |
| Flash point | 113 °C (235 °F; 386 K) |
| Related compounds | |
Related compounds
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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
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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.[3]
Mandelonitrile can break down into cyanide and benzaldehyde, a reaction that can be catalyzed 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:[4]
References edit
- ^ Sigma-Aldrich product page
- ^ a b The Merck Index (12th ed.). 1996.
- ^ 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". Organic Syntheses; Collected Volumes, vol. 1, p. 336.