6641-60-7

Usage

Molecular structure

2-(3,5-dimethylphenoxy)benzoic acid consists of a benzoic acid molecule with a phenoxy group attached at the 2-position, with two methyl groups attached at the 3 and 5 positions of the phenoxy group.

Usage

It is commonly used as an ingredient in herbicides and plant growth regulators due to its ability to inhibit the growth of unwanted plants. It is also used in the synthesis of various pharmaceutical compounds and as a building block in organic chemistry.

Potential properties

2-(3,5-dimethylphenoxy)benzoic acid has been studied for its potential anti-inflammatory and anti-cancer properties.

Upstream product

• 16497-87-3 potassium o-bromobenzoate 
• 108-68-9 3,5-Dimethylphenol 
• 1040310-52-8 2-(3,5-dimethylphenoxy)benzonitrile 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 108059-55-8 2-(3,5-Dimethyl-phenoxy)-benzoic acid methyl ester 
• 108059-54-7 2-(2-Acetyl-3,5-dimethylphenoxy)benzoesaeure-methylester 

Relevant academic research and scientific papers

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.

Dibenzocyclooctene-, Dibenzochalcocine-, and Diarenochalconinediones

2,2'-Oxybis-, -thiobis-, and -methylenebisbenzoic esters 2a-c react with methyllithium in ether to give low yields of 5H-dibenzochalcocine-5,7(6H)-diones 6a, 7a, and dibenzocyclooctene-5,7(6H,12H)-dione (8), respectively.Very good yields of such heterocycles with oxygen (6a-h, 37), sulfur (7a-h, 38) and selenium (36) as key atom are obtained when diaryl ethers (21, 22, 25), -sulfides (27, 29, 30), and -selenides (33) that contain 2'-acetyl- (or -propionyl-) and 2-methoxycarbonyl groups are treated with sodium hydride in boiling toluene.Analogously are prepared the dibenzoxonine-11,13(6H,12H)diones 62a-c and 7H-benzonaphthothionine-7,9-(8H)-dione (65) which are expanded by one ring member.In the analogous reaction of a corresponding benzophenone derivative 35, spiro-3(2H),3'-dione (41) is formed in a tandem reaction. - Under phase transfer conditions the dibenzochalcocinediones 6, 7, 36 and also the corresponding nitrogen cycles 5 react to give mixtures of C- (42-45) and O-alkyl derivatives (46-49).Methyllithium and diisobutylaluminium hydride provide the carbinols 50-54.With bromine and SO2Cl2, respectively, the methylene group is mono- or dihalogenated to the products 56, 57; defined nitration was only possible for the oxacycle 6a.