3-Phenoxybenzaldehyde

Chemical properties

clear light yellow to amber liquid, insoluble in water, soluble in alcohol, benzene, toluene and other organic solvents.

The Uses of 3-Phenoxybenzaldehyde

3-phenoxybenzaldehyde is an important intermediate for the synthesis of pyrethroid pesticides phenothrin, cypermethrin, deltamethrin,fenvalerate, fenpropathrin, flucythrinate, cyhalothrin, etc.

Preparation

Synthesis of 3-Phenoxybenzaldehyde: 3-phenoxybenzoic acid is generated by catalytic oxidation of 3-phenoxytoluene, followed by electrolytic reduction to obtain Phenoxybenzyl alcohol , and then selective oxidation with sodium hypochlorite to obtain 3-Phenoxybenzaldehyde.

Production Methods

3-Phenoxybenzaldehyde is prepared by adding, at a relatively low temperature, a mixture of a 3-phenoxybenzyl halide and a 3-phenoxybenzal halide to a mixture of hexamethylenetetramine, acetic acid and water, the amounts of the water and acid bearing certain relationships to the amount of the mixture of halides, then heating the resulting mixture to a specified temperature level and maintaining it at that level for a specified period of time.
https://patents.google.com/patent/US4229380A/en

General Description

Enantioselective autoinduction during asymmetric hydrocyanation of 3-phenoxybenzaldehyde catalyzed by cyclo[(R)-phenylalanyl-(R)-histidyl] has been investigated. It undergoes hydrogenation catalyzed by Au/Pt bimetallic core/shell nanoparticles to yield 3-phenoxyphenyl methanol.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating vapors.

Degradation

3-Phenoxybenzoic acid(3-PBA) and 3-phenoxybenzaldehyde are the most common intermediates in the degradation pathways of Type Il pyrethroids by bacteria, except the cyfluthrin degradation in Brevibacterium aureum DG-12, the beta-cyfluthrin degradation in Pseudomonas stutzeri S1, and the fenpropathrin degradation in Clostridium sp. ZP3(Chen et al.2013a; Saikia et al.2005;Zhang et al.2011b).