(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile
CAS: 61826-76-4;122395-47-5
Molecular Formula: C14H11NO2
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile - Names and Identifiers
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile - Physico-chemical Properties
| Molecular Formula | C14H11NO2 |
| Molar Mass | 225.24 |
| Density | 1.220±0.06 g/cm3(Predicted) |
| Boling Point | 399.8±32.0 °C(Predicted) |
| Flash Point | 195.609°C |
| Vapor Presure | 0mmHg at 25°C |
| pKa | 10.33±0.20(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.607 |
| Physical and Chemical Properties | Chemical quality This product is an oily liquid,[α]25D =-24.81 °(Cl,CHCl3), soluble in benzene, toluene, ethyl acetate, n-hexane and other organic solvents. |
| Use | Application S-α-cyano-3-phenoxybenzyl alcohol (S-cyanohydrin) is an important intermediate for the preparation of S,S-fenvalerate, zeta-cypermethrin and deltamethrin. |
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile - Production method
The preparation method is to esterify racemic 2-cyano-3-phenoxybenzyl alcohol with acetic anhydride or acetyl chloride into the corresponding acetate, and then carry out selective hydrolysis in the presence of lipase. The S body is hydrolyzed to generate S-cyanol, while the R body still maintains the structure of acetate. After separation, R-α-cyano-3-phenoxybenzyl acetate is racified and hydrolyzed in the presence, S-cyanohydrin, repeated application, S-α-cyano-3-phenoxybenzyl alcohol [α]D = 33 °(CCl4).
The racemic α-cyano-3-phenoxybenzyl alcohol can also be heated with the bicyclic body of 1R ciscarylic acid in the presence of an acid catalyst to form two ether diastereomers, one of which is R-The enantiomer of the configuration is an oil, and the enantiomer of the other S-configuration is a crystal. After separation, the latter undergoes acidic hydrolysis to obtain the bicyclic body of S-cyanide and resolution agent 1R cis-carylic acid.
It is also possible to use 3, 5-disubstituted hyphenin and cyclic dipeptide for the synthesis of S-α-cyano-3-phenoxybenzyl alcohol.
Last Update：2024-04-10 22:29:15
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile - Reference Information
| Introduction | (S)-(3-phenoxyphenyl) hydroxyacetonitrile is a pesticide intermediate that can be used to prepare flufenothrin. Cyanthrin is mainly used in cotton, fruit trees, vegetables, corn, tea, tobacco and other crops, including Lepidoptera, Coleoptera, Homoptera, Diptera and Thysanoptera, etc. The main pest control is also effective for sanitary pests such as houseflies, Culex pipiens, and Blattella germanica. Compared with other pyrethroids, it has a significant acaricidal effect. |
| Application | (S)-(3-phenoxyphenyl) hydroxyacetonitrile is a pesticide intermediate that can be used to prepare flufenothrin. |
| synthesis method | first add 0.5g(1.88mmol) of S-cyanohydrin acetate to the triangular flask, then add 87ul(0.94mmol)BuOH, 0.05mg of antarctic candida lipase (NOVO 435) and 10ml of isopropyl ether to the shaking table at 10 ℃ for 72h. Then, after the reaction solution is concentrated and dried, the reaction solution is dissolved with 20ml of mixed solution (composed of 6ml of water, 14ml of methanol and 6ml of benzene), the lower layer solution is taken by liquid separation, the reaction solution is extracted with 10ml of mixed solution of benzene and methanol (the volume ratio of benzene to methanol is 7:3) for the second time, part of methanol is evaporated, and EA is added to remove the water layer, the EA layer was dried and concentrated to obtain 0.06g of (S)-(3-phenoxyphenyl) hydroxyacetonitrile. |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Last Update：2024-04-09 21:54:55
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