alpha-Hydroxy-3-phenoxybenzeneacetonitrile (alphaS)-

alpha-Hydroxy-3-phenoxybenzeneacetonitrile (alphaS)- - Names and Identifiers

Name	(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile
Synonyms	(s)-benzeneacetonitril Deltamethrin Impurity 5 S-α-cyano-3-phenoxy benzyl alcohol (S)-3-PHENOXYBENZALDEHYDE CYANOHYDRIN (S)-3-Phenoxybenzaldehyde cyanohydrin (S)-3-Phenoxybenzaldehydecyanohydrine (s)-alpha-cyano-m-phenoxybenzylalcohol (s)-alpha-cyano-3-phenoxybenzylalcohol (S)-Cyanohydrine metaphenoxy benzaldehyde (2S)-hydroxy(3-phenoxyphenyl)ethanenitrile (S)-(-)-alpha-Cyano-3-phenoxybenzyl alcohol (S)-alpha-Hydroxy-3-phenoxybenzeneacetonitrile Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (S)- alpha-Hydroxy-3-phenoxybenzeneacetonitrile (alphaS)- Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-
CAS	61826-76-4 122395-47-5
InChI	InChI=1/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

alpha-Hydroxy-3-phenoxybenzeneacetonitrile (alphaS)- - 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.

alpha-Hydroxy-3-phenoxybenzeneacetonitrile (alphaS)- - 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

alpha-Hydroxy-3-phenoxybenzeneacetonitrile (alphaS)- - 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