43192-09-2

Basic information

• Product Name: 3-chloro-2-methylphenylhydroxylamine
• Synonyms: 3-chloro-2-methylphenylhydroxylamine
• CAS NO: 43192-09-2
• Molecular Weight: 157.6
• Mol File: 43192-09-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-chloro-2-methylphenylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-2-methylphenylhydroxylamine(43192-09-2)
• EPA Substance Registry System: 3-chloro-2-methylphenylhydroxylamine(43192-09-2)

Safety Data

• Hazardous Substances Data: 43192-09-2(Hazardous Substances Data)

Upstream product

• 83-42-1 6-chloro-2-nitrotoluene 

Downstream Products

• 3096-68-2 4-Amino-2-chlor-3-methyl-phenol 

Relevant articles and documents

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Kinetics and Mechanism of the Bamberger Rearrangement. Part 4. Rearrangement of Sterically Hindered Phenylhydroxylamines to 4-Aminophenols in Aqueous Sulphuric Acid Solution

The rates of the Bamberger rearrangement of sterically hindered phenylhydroxylamines have been determined in aqueous sulphuric acid solution and the substituent effects (in particular, the steric effects) are discussed.The rate constants for phenylhydroxylamines with 2-substituents (Me, Cl, I) satisfied the Taft equation: log krel = ρ*?* - δES with ρ*-1.93 and δ-1.16.The result shows that steric hindrance of the substituents, in addition to the electron-donating effect, has an accelerating effect on the rates of the Bamberger rearrangement.The rate constants for 3-substituted 2-methylphenylhydroxylamines were generally greater than those for 5-substituted 2-methylphenylhydroxylamines.The difference was attributed to the 'buttressing effect' of neighbouring 3-substituents.This is the first example of steric acceleration of the Bamberger rearrangement.