Mandelonitrile

Mandelonitrile^[1]
Names
	IUPAC name 2-Hydroxy-2-phenylacetonitrile
	Other names α-Hydroxybenzeneacetonitrile
Identifiers
CAS Number	532-28-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2207122
ChEBI	CHEBI:16910 ;
ChEMBL	ChEMBL1393845;
ChemSpider	10304 ;
ECHA InfoCard	100.007.758
EC Number	208-532-7;
Gmelin Reference	1684586
KEGG	C00561 ;
PubChem CID	10758;
UNII	584322E08A ;
UN number	2810
CompTox Dashboard (EPA)	DTXSID2025422 ;
	InChI InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H Key: NNICRUQPODTGRU-UHFFFAOYSA-N ; InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H Key: NNICRUQPODTGRU-UHFFFAOYAG;
	SMILES 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)
Boiling point	282.70 °C (540.86 °F; 555.85 K) Decomposes
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). verify (what is ?) Infobox references

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. Prunasin can be hydrolyzed by the enyzme prunase into glucose and mandelonitrile (for example, when an appleseed is digested in a ruminant's stomach).

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

^ 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.

[SA-1] Sigma-Aldrich product page

[merck-2] 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

[Corson-4] Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Organic Syntheses; Collected Volumes, vol. 1, p. 336.

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