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;
ChEBI	CHEBI:16910 ;
ChemSpider	10304 ;
ECHA InfoCard	100.007.758
KEGG	C00561 ;
PubChem CID	10758;
	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	133.15 g·mol−1
Density	1.117 g/mL
Melting point	−10 °C (14 °F; 263 K) (R/S)[2]
Boiling point	170 °C (338 °F; 443 K) Decomposes[2]
Hazards
Main hazards	toxic
R-phrases (outdated)	R23/24/25 R36/37/38 R41
S-phrases (outdated)	S22 S26 S36/37/39 S45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).
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	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.

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
1 2 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. ; Collective Volume, 1, p. 336

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[SA-1] Sigma-Aldrich product page

[merck-2] 1 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. ; Collective Volume, 1, p. 336