6325-68-4

Usage

Uses

Used in Organic and Pharmaceutical Synthesis:
2-(2-METHYLPHENOXY)BENZOIC ACID is used as a key intermediate in the synthesis of various organic and pharmaceutical compounds due to its unique chemical structure and reactivity.
Used in Dyes and Pigments Production:
2-(2-METHYLPHENOXY)BENZOIC ACID is used as a raw material in the production of dyes and pigments, contributing to their color and stability.
Used in Medicinal Compounds Development:
2-(2-METHYLPHENOXY)BENZOIC ACID is used as a potential candidate for the development of new medicinal compounds, owing to its anti-inflammatory and analgesic properties.
Used in Crop Protection Products:
2-(2-METHYLPHENOXY)BENZOIC ACID is used in the manufacturing of crop protection products and herbicides, due to its herbicidal and fungicidal activities, which help protect crops from pests and diseases.

InChI:InChI=1/C18H20N2O2S2/c1-12-6-8-13(9-7-12)10-15-17(22)20(18(23)24-15)11-16(21)19-14-4-2-3-5-14/h6-10,14H,2-5,11H2,1H3,(H,19,21)/b15-10-

Upstream product

• 95-48-7 ortho-cresol 
• 118-91-2 ortho-chlorobenzoic acid 
• 59167-50-9 ethyl 2-(o-tolyloxy)benzoate 
• 394-47-8 2-fluorobenzonitrile 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 1488-42-2 Diphenyliodonium-2-carboxylate 
• 142-71-2 copper diacetate 
• 88-67-5 2-Iodobenzoic acid 
• 16463-38-0 potassium 2-chlorobenzoate 

Downstream Products

• 5396-28-1 4-methylxanthen-9-one 
• 37424-29-6 2,2'-oxybis(benzoic acid) 
• 120041-63-6 2-o-Tolyloxy-benzoyl chloride 
• 144463-71-8 allyl 2-(2-methylphenoxy)benzoate 
• 32852-70-3 2,2'-oxy-di-benzoyl chloride 
• 393869-33-5 O(C₆H₄CONC₆H₁₄)2 
• 154420-61-8 N-(4-methyl-9H-xanthen-9-yl)-2-chloroethanamide 
• 31680-22-5 2,2'-Oxybisbenzoesaeure-dimethylester 
• 7320-53-8 4-methyl-dibenzofuran 
• 3991-61-5 1-methyl-2-phenoxybenzene 

Relevant academic research and scientific papers

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.

Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution

Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.

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.

Design, synthesis and insecticidal activity of diamides with oxydibenzene or diphenylamine subunits

Introduction: After using insecticides over many years, the resistance and environmental issues have become great challenges to crop protection. Modern agriculture calls for new insecticidal candidates. Phthalic diamide insecticide containing adjacent two amide group were favored for its new mode of action. Most chemical optimizations of phthalic diamide insecticide focused on amide groups. Modifications on phenyl part including fewer substituent types. Objective: The objective of this article was to investigate the insecticidal activities variation by alter the orientation and distance of two amide by replace the phenyl part with oxydibenzene and diphenyl-amine. Results: The target compounds were synthesized by using Cu/CuI catalyzed Ullmann coupling and sulfonyl-O-acryl mixed-anhydride as reactive intermediate. All target compounds were evaluated against armyworm (Mythimna sepatara). Two of synthetic compounds containing multifluoro-alkoxyl substituent showed mortality rate of 100% at 500 mg L-1. DFT-based Potential energy surface scanning showed that the relative energies of three conformations of insecticidal compounds were very similar Conclusion: We designed, synthesized and characterized seventeen novel compounds for the insecticidal candidates. Two of them were found to be insecticidal. A preliminary structure-activity relationship showed that the multifluoro-alkoxyl groups on the benzene were preferred. The compound d5 could be a lead compound for further research.

A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids

We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.

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.

Photodecarboxylation of xanthone acetic acids: C-C bond heterolysis from the singlet excited state

Irradiation of 2- and 4-xanthone acetic acid in aqueous buffer (pH 7.4) leads to efficient (Φ = 0.67 and 0.64, respectively) photodecarboxylation to give the corresponding methyl products, consistent with an intermediate benzylic carbanion. Fluorescence a

Microwave-assisted synthesis of 2-phenoxybenzoic acids

Substituted 2-phenoxybenzoic acid derivatives were synthesised in high yield and in short reaction times using the Ullmann condensation of 2-chlorobenzoic acid with phenol derivatives under microwave irradiation in dry media.

The use of ultrasound in the synthesis of 2-carboxy substituted diphenylethers using water as solvent

An improved synthesis of 2-carboxy substituted diphenylethers using water as solvent can be achieved by ultrasound irradiation. A number of diphenylethers was prepared in good yields in a very short reaction time.