3-Phenoxymandelonitrile

3-Phenoxymandelonitrile
Identifiers
CAS Number	61826-76-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	8013157;
ECHA InfoCard	100.052.566
EC Number	441-070-6;
PubChem CID	9837437;
CompTox Dashboard (EPA)	DTXSID00885773 ;
	InChI InChI=1S/C14H11NO2/c15-10-14(16)11-5-4-8-13(9-11)17-12-6-2-1-3-7-12/h1-9,14,16H/t14-/m1/s1 Key: GXUQMKBQDGPMKZ-CQSZACIVSA-N;
	SMILES C1=CC=C(C=C1)OC2=CC=CC(=C2)[C@@H](C#N)O;
Properties
Chemical formula	C14H11NO2
Molar mass	225.247 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H301, H317, H318, H410
Precautionary statements	P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-phenoxymandelonitrile (also 3-phenoxy-α-cyanobenzyl alcohol) is an organic compound belonging to the group of cyanohydrins. It is primarily used in the synthesis of pyrethroids, a class of insecticides.

Production

The synthesis of 3-phenoxymandelonitrile begins with the reaction of 3-phenoxybenzaldehyde with sodium cyanide and acetic anhydride in a water/dichloromethane mixture, using benzyltriethylammonium chloride as a phase transfer catalyst. This reaction initially produces the acetate, which can be hydrolyzed enzymatically with a suitable lipase to yield enantiomerically pure (S)-3-phenoxymandelonitrile through chiral resolution.^[2] The desired product can be extracted at this stage. The remaining enantiomeric acetate can undergo racemization via reaction with triethylamine in toluene or diisopropyl ether to improve yield.^[3] An alternative synthesis involves transferring a cyano group from acetone cyanohydrin to 3-phenoxybenzaldehyde. Again, enzymatic reactions through an ester can be used to produce the enantiomerically pure compound.^[4]

Use

(S)-3-Phenoxymandelonitrile serves as an important intermediate in the production of various pyrethroids, which are carboxylic acid esters incorporating the compound as an alcohol component, and are employed as insecticides.^[2]^[3] Notable examples within this group include deltamethrin and esfenvalerate.^[2] The presence of the 3-phenoxy group and nitriles enhances the efficacy of these compounds compared to other pyrethroids.^[5]

References

^ "(S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b ^c Ayelet Fishman, Michael Zviely (January 1998), "Chemo-enzymatic synthesis of (S)-α-cyano-3-phenoxybenzyl alcohol", Tetrahedron: Asymmetry, vol. 9, no. 1, pp. 107–118, doi:10.1016/S0957-4166(97)00608-3
^ ^a ^b Yongjin Chen, Jianping Wu, Gang Xu, Lirong Yang (October 2006), "Separation of α-cyano-3-phenoxybenzyl alcohol from α-cyano-3-phenoxybenzyl acetate using solvent extraction", Separation and Purification Technology, vol. 51, no. 3, pp. 424–429, doi:10.1016/j.seppur.2006.03.006{{citation}}: CS1 maint: multiple names: authors list (link)
^ Tingzhou Zhang, Lirong Yang, Ziqiang Zhu, Jianping Wu (October 2002), "The kinetic study on lipase-catalyzed transesterification of α-cyano-3-phenoxybenzyl alcohol in organic media", Journal of Molecular Catalysis B: Enzymatic, vol. 18, no. 4–6, pp. 315–323, doi:10.1016/S1381-1177(02)00112-1{{citation}}: CS1 maint: multiple names: authors list (link)
^ Takamitsu Kobayashi, Keiichiro Nishimura, Toshio Fujita (November 1989), "Effects of the α-cyano group in the benzyl alcohol moiety on insecticidal and neurophysiological activities of pyrethroid esters", Pesticide Biochemistry and Physiology, vol. 35, no. 3, pp. 231–243, Bibcode:1989PBioP..35..231K, doi:10.1016/0048-3575(89)90084-9{{citation}}: CS1 maint: multiple names: authors list (link)

[1] "(S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile". pubchem.ncbi.nlm.nih.gov.

[Ayelet_1998-2] Ayelet Fishman, Michael Zviely (January 1998), "Chemo-enzymatic synthesis of (S)-α-cyano-3-phenoxybenzyl alcohol", Tetrahedron: Asymmetry, vol. 9, no. 1, pp. 107–118, doi:10.1016/S0957-4166(97)00608-3

[:1-3] Yongjin Chen, Jianping Wu, Gang Xu, Lirong Yang (October 2006), "Separation of α-cyano-3-phenoxybenzyl alcohol from α-cyano-3-phenoxybenzyl acetate using solvent extraction", Separation and Purification Technology, vol. 51, no. 3, pp. 424–429, doi:10.1016/j.seppur.2006.03.006{{citation}}: CS1 maint: multiple names: authors list (link)

[4] Tingzhou Zhang, Lirong Yang, Ziqiang Zhu, Jianping Wu (October 2002), "The kinetic study on lipase-catalyzed transesterification of α-cyano-3-phenoxybenzyl alcohol in organic media", Journal of Molecular Catalysis B: Enzymatic, vol. 18, no. 4–6, pp. 315–323, doi:10.1016/S1381-1177(02)00112-1{{citation}}: CS1 maint: multiple names: authors list (link)

[5] Takamitsu Kobayashi, Keiichiro Nishimura, Toshio Fujita (November 1989), "Effects of the α-cyano group in the benzyl alcohol moiety on insecticidal and neurophysiological activities of pyrethroid esters", Pesticide Biochemistry and Physiology, vol. 35, no. 3, pp. 231–243, Bibcode:1989PBioP..35..231K, doi:10.1016/0048-3575(89)90084-9{{citation}}: CS1 maint: multiple names: authors list (link)

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