6338-04-1

Usage

Physical state

Yellow crystalline powder

Solubility

Insoluble in water, soluble in organic solvents

Uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Potential applications

Treatment of various diseases (including cancer and inflammatory conditions), antioxidant properties (potential use in dietary supplements and skincare products)

InChI:InChI=1/C14H12O3/c1-10-5-4-6-11(9-10)17-13-8-3-2-7-12(13)14(15)16/h2-9H,1H3,(H,15,16)

Upstream product

• 16463-38-0 potassium 2-chlorobenzoate 
• 108-39-4 3-methyl-phenol 
• 118-91-2 ortho-chlorobenzoic acid 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 620-46-2 3'-methylphenyl salicylate 
• 341035-15-2 2,3'-oxy-di-benzoyl chloride 
• 120041-62-5 N-Phenoxy-2-m-tolyloxy-benzamide 
• 120041-58-9 N-Methoxy-2-m-tolyloxy-benzamide 
• 7133-57-5 N-(m-methylphenyl)salicylamide 
• 7320-50-5 1-methyl-dibenzofuran 
• 7320-52-7 3-methyldibenzo[b,d]furan 
• 85636-86-8 methyl 9-oxo-9H-xanthene-1-carboxylate 
• 144463-69-4 allyl 2-(3-methylphenoxy)benzoate 
• 120041-64-7 2-m-Tolyloxy-benzoyl chloride 
• 74302-25-3 2-(3-carboxyphenoxy)benzoic acid 
• 19814-98-3 3-methyl-9H-xanthen-9-one 
• 84273-41-6 1-Methyl-9H-xanthen-9-one 

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.

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.

Synthesis and antiproliferative activity of substituted benzopyranoisoindoles: A new class of cytotoxic compounds

A series of novel aminosubstituted benzopyranoisoindoles possessing structural analogy to an active nitracrine metabolite are reported. The compounds exhibited interesting cytotoxic activity against a panel of cell lines, which was maximized by the presen

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.

Substituted xanthones as antimycobacterial agents*, part 1: Synthesis and assignment of 1H/13C NMR chemical shifts

A series of substituted xanthones was synthesized in order to prove the hypothesis that electron-withdrawing substituents enhance the antimycobacterial activity of these compounds, which is described by means of a QSAR equation with 13C NMR che

Use of pyridine as cocatalyst for the synthesis of 2-carboxy substituted diphenylethers by Ullmann-Goldberg condensation

The synthesis of 2-carboxy-diphenylethers from o-chloro-benzoic acid and phenols is reported using water as solvent and copper, cuprous iodide and pyridine as catalysts.

Gas phase generation and cyclisation reactions of some o-substituted phenyl radicals

Flash vacuum pyrolysis of the allyl esters 2 (X=O, S, CH2, CO) at 900°C (10-2 Torr) gives dibenzofurans, dibenzothiophenes, fluorenes, and fluorenones respectively as the major products. The mechanism involves the phenyl radical intermediates 1 which equilibrate by intramolecular hydrogen transfer via six-membered transition states, prior to cyclisation.