2918-88-9

Basic information

• Product Name: 4-(Phenylazo)benzoic acid methyl ester
• Synonyms: 4-(Phenylazo)benzoic acid methyl ester;Azobenzene-4-carboxylic acid methyl ester
• CAS NO: 2918-88-9
• Molecular Formula: C₁₄H₁₂N₂O₂
• Molecular Weight: 0
• Mol File: 2918-88-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 382.1°C at 760 mmHg
• Flash Point: 174.5°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 4.84E-06mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 4-(Phenylazo)benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Phenylazo)benzoic acid methyl ester(2918-88-9)
• EPA Substance Registry System: 4-(Phenylazo)benzoic acid methyl ester(2918-88-9)

Safety Data

• Hazardous Substances Data: 2918-88-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12N2O2/c1-18-14(17)11-7-9-13(10-8-11)16-15-12-5-3-2-4-6-12/h2-10H,1H3/b16-15+

Upstream product

• 137720-88-8 4-(2-phenylhydrazino)benzoic acid methyl ester 
• 186581-53-3 diazomethane 
• 1562-93-2 4-(2-phenyldiazen-1-yl)benzoic acid 
• 70712-85-5 1-phenyl-2,2-dimethyl-1-propyl bromide 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 104-24-5 4-phenylazobenzoyl chloride 
• 3517-24-6 4-Benzolazo-benzoyl-malonsaeurediethylester 

Downstream Products

• 108163-90-2 1-t-butyl-2-(4-methoxycarbonylphenyl)-1-phenylhydrazine 
• 108163-89-9 1-t-butyl-1-(4-methoxycarbonylphenyl)-2-phenylhydrazine 
• 137720-88-8 4-(2-phenylhydrazino)benzoic acid methyl ester 
• 67661-53-4 methyl 2-phenyl-2H-benzo[d][1,2,3]triazole-5-carboxylate 

Relevant articles and documents

TEMPO catalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

A metal-free direct oxidative dehydrogenation approach for the synthesis of azobenzenes from hydrazobenzenes has been developed by using TEMPO as an organocatalyst for the first time. The reaction proceeded in open air under mild reaction conditions. A wide range of hydrazobenzenes readily undergo dehydrogenation to give the corresponding azobenzenes in excellent yields.

The Nucleophilicity of Superoxide towards Different Alkyl Halides Estimated from Kinetic Measurements

Values of the rate constant ksub are measured for the substitution reaction between superoxide O2 anion-radical and the alkyl halides butyl chloride, 2-butyl chloride, benzyl chloride, ethyl bromide, butyl bromide, 2-butyl bromide, neopentyl bromide, benzyl bromide, (1-bromo-2,2-dimethylpropyl)benzene and 1-iodoadamantane.These rate constants are compared with the expected rate constant kET for the electron transfer reaction between the same alkyl halides and an aromatic anion radical A anion-radical with the same standard oxidation potential as O2 anion-radical.The ksub/kET ratios show that the mechanism of the substitution reaction amy shift from SN2-like to ET-like on changes in the steric hindrance and the acceptor ability of the alkyl halide.The influence on ksub/kET of the difference in self-exchange reorganization energy λ(0) between O2 anion-radical/O2 and A anion-radical/A is discussed.

Single Electron Transfer as Rate-Determining Step in an Aliphatic Nucleophilic Substitution

The rate of transfer of an electron between electrochemically generated anion radicals and alkyl halides has been measured by cyclic voltammetry and the dependence of the rate on the redox potential of the electron donors found.From this dependence, the rate of electron transfer from an electron donor with reorganization energy about 10 kcal mol-1 to a given alkyl halide can be calculated if the reversible oxidation potential of the donor is known.The method has been applied to show that the rate of the aliphatic nucleophilic substitution of the enolate ion of 4-methoxycarbonyl-4-methyl-1,4-dihydropyridine on t-butyl bromide, neopentyl bromide and adamantyl bromide is the same as that expected for a SET reaction for a donor with the same oxidation potential as the enolate ion.Primary alkyl halides react somewhat faster than expected for a pure SET reaction.The dianion of dihydroperylene reacts with t-butyl chloride and s-butyl bromide at the same rate as would be expected for a SET reaction with a donor with the same oxidation potential as the dianion.The model for the aliphatic nucleophilic substitution is discussed.