50699-52-0

Upstream product

• 1885-14-9 phenyl chloroformate 
• 99-09-2 3-nitro-aniline 
• 3320-87-4 isocyanic acid (3-nitro-phenyl) ester 
• 108-95-2 phenol 
• 3532-31-8 3-nitrobenzoyl azide 
• 618-94-0 3-nitrobenzoic acid hydrazide 

Downstream Products

• 68621-59-0 (3-amino-phenyl)-carbamic acid phenyl ester 
• 17433-92-0 N-(3-nitrophenyl)hydrazinecarbamide 
• 22197-11-1 N,N'-m-phenylene-bis-carbamic acid diphenyl ester 

Relevant academic research and scientific papers

Azobenzene-Semicarbazone Enables Optical Control of Insect Sodium Channels and Behavior

Photopharmacology uses molecular photoswitches to establish control over the action of bioactive molecules. The application of photopharmacology in the research of invertebrate sodium channels has not been investigated. Here we report several photochromic ligands of metaflumizone. One ligand, termed ABM04, underwent reversible trans-cis isomerization under ultraviolet or blue light irradiation. cis-ABM04 had excellent larvicidal activity against mosquito larvae with an LC50 value of 4.39 μM and showed insecticidal activity against Mythimna separata with an LC50 value of 7.19 μM. However, trans-ABM04 was not found to have biological activity. ABM04 (10 μM) can induce depolarization of dorsal unpaired median neurons and enable the real-time photoregulation of mosquito larval behavior. The precise regulation of invertebrate sodium channels is realized for the first time, which provides a new strategy for the basic and accurate research of invertebrate sodium channels.

Nucleophilic substitution reactions of phenyl chloroformates

Methanolysis and aminolysis of phenyl chloroformates in acetonitrile have been investigated.The rates are slow due to initial-state stabilization by strong resonance electron donation from the phenoxy group.In both reactions the large positive values of ρY = 0.8-1.6 and low ΔH(excit.) and ΔS(excit.) values show that the transition state is strongly associative with little bond breaking.This mechanism is supported by the relatively large solvent isotope effect, kMeOH/kMeOD = ca. 2.3-2.5, and by the relatively strong inverse secondary kinetic isotope effect, kH/kD =/ca. 0.74-0.94, involving deuteriated aniline nuclephiles, in addition to a negative value of ρXY.The dependence on aniline basicity, βx(βnuc) =/ca. 0.8, and the ρX values of -2.3 are similar to those corresponding values for the reactions of benzoyl chlorides which have been predicted to react by an associative SN2 mechanism.These observations are consistent with a concerted displacement mechanism for the methanolysis and aminolysis of phenyl chloroformates.