3-Phenoxymandelonitrile
Chemical compound
From Wikipedia, the free encyclopedia
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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| Names | |
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| Preferred IUPAC name
(2S)-Hydroxy(3-phenoxyphenyl)acetonitrile | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.052.566 |
| EC Number |
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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 |
| Hazards | |
| GHS labelling:[1] | |
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| Warning | |
| 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
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]
