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3-Phenoxymandelonitrile

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3-Phenoxymandelonitrile
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.052.566 Edit this at Wikidata
EC Number
  • 441-070-6
PubChem CID
CompTox Dashboard (EPA)
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/s1Key: GXUQMKBQDGPMKZ-CQSZACIVSA-N
SMILES
  • C1=CC=C(C=C1)OC2=CC=CC(=C2)(C#N)O
Properties
Chemical formula C14H11NO2
Molar mass 225.247 g·mol
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
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 , 100 kPa). Infobox references
Chemical compound

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. 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. 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.

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. Notable examples within this group include deltamethrin and esfenvalerate. The presence of the 3-phenoxy group and nitriles enhances the efficacy of these compounds compared to other pyrethroids.

Deltamethrin, an ester of 3-phenoxymandelonitrile used as an insecticide

References

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