6410-65-7

Basic information

• Product Name: 2-(4-chlorophenoxy)benzoic acid
• Synonyms: 2-(4-chlorophenoxy)benzoic acid
• CAS NO: 6410-65-7
• Molecular Formula: C₁₃H₉ClO₃
• Molecular Weight: 248.66176
• Mol File: 6410-65-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-chlorophenoxy)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenoxy)benzoic acid(6410-65-7)
• EPA Substance Registry System: 2-(4-chlorophenoxy)benzoic acid(6410-65-7)

Safety Data

• Hazardous Substances Data: 6410-65-7(Hazardous Substances Data)

Usage

Class

Benzoic acid derivatives

Common use

Herbicide

Function

Inhibits growth of broadleaf plants by interfering with growth hormones

Usage

Agricultural and horticultural industries for weed control in crops and gardens

Chemical structure

Benzoic acid molecule with a 4-chlorophenoxy group attached

Selectivity

Potent and selective herbicide

Mammalian toxicity

Low

Upstream product

• 106-48-9 4-chloro-phenol 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 394-47-8 2-fluorobenzonitrile 
• 146537-85-1 2-(4-chlorophenoxy)-benzonitrile 
• 16463-38-0 potassium 2-chlorobenzoate 

Downstream Products

• 25562-90-7 2-<4-Chlorphenyloxy>-benzylalkohol 
• 13210-15-6 2-chloroxanthen-9-one 
• 25562-95-2 4-chloro-2'-chloromethyldiphenyl ether 
• 25958-86-5 2-(4-chlorophenoxy)phenylacetonitrile 
• 1221277-38-8 N-(4-chlorophenyl)-2-hydroxy-N-methylbenzamide 
• 2944-58-3 4-chlorophenyl 2-hydroxybenzoate 
• 25563-04-6 o-(p-chlorophenoxy)phenylacetic acid 
• 51230-49-0 2-chlorodibenzofuran 
• 144463-67-2 allyl 2-(4-chlorophenoxy)benzoate 

Relevant articles and documents

Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation

A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.

Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis

We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.

Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement

We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.