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.
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.052.566 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C14H11NO2 | |
| Molar mass | 225.247 g·mol−1 |
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| H301, H317, H318, H410 | |
| 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).
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Production
editThe 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
edit(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
edit- ^ "(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)