131323-10-9

Usage

Uses

Used in Pharmaceutical Industry:
2,2-Difluoro-2-p-tolylacetic acid is used as an intermediate for the synthesis of various biologically active compounds, contributing to the development of new drugs and enhancing the therapeutic potential of existing medications.
Used in Agrochemical Industry:
In the agrochemical sector, 2,2-Difluoro-2-p-tolylacetic acid serves as a key intermediate in the production of agrochemicals, aiding in the creation of effective and targeted pest control solutions.
Used in Medicinal Chemistry:
2,2-Difluoro-2-p-tolylacetic acid is utilized as a synthetic intermediate in medicinal chemistry, facilitating the design and synthesis of novel compounds with potential therapeutic applications.

Upstream product

• 624-31-7 4-tolyl iodide 
• 667-27-6 Ethyl bromodifluoroacetate 
• 106-49-0 p-toluidine 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 131323-06-3 α,α-difluoro-4-methylbenzeneacetic acid ethyl ester 

Downstream Products

• 127152-96-9 (+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid 

Relevant academic research and scientific papers

Copper-catalyzed cascade radical cyclization of alkynoates: Construction of aryldifluoromethylated coumarins

A mild and simple method is reported for the construction of 3-difluoroarylmethylated coumarins using α,α-difluoroarylacetic acids as an easily handled difluoromethyl source in reaction with ester 3-arylpropiolates under the promotion of copper. The reaction involves a proposed radical-triggered domino decarboxylative aryldifluoromethylation/5-exo cyclization/ester migration process that directly forms Csp2-CF2Ar and C-C bonds with good functional group tolerance. This journal is

Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds

An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.

Silver-Catalyzed Decarboxylative Alkynylation of α,α-Difluoroarylacetic Acids with Ethynylbenziodoxolone Reagents

A decarboxylating alkynylation of α,α-difluoroarylacetic acids with ethynylbenziodoxolone reagents is reported. AgNO3 serves as the catalyst and K2S2O8 as the oxidant. A series of functional groups were tolerated, and moderate to good yields were obtained.

Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination

An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.

Carboxylic Acids and Tetrazoles as Isosteric Replacements for Sulfate in Cholecystokinin Analogues

A series of analogues of the satiely-inducing peptide cholecystokinin (CCK-8) was prepared in which the sulfated tyrosine required for activation of peripheral receptors was replaced with a carboxy(alkyl)- or tetrazolyl(alkyl)-phenylalanine to investigate whether an organic acid could serve the role of the sulfate group at the receptor.The necessary intermediates were prepared by previously reported procedures or by alkylation of carboxy(alkyl)- or tetrazolyl(alkyl)phenylmethyl bromides with a glycine-derived anion followed by protecting-group manipulations, and these were incorporated into derivatives of acetyl-CCK-7 using solid-phase synthesis.Peptide analogues were evaluated in a CCK-binding assay for affinity for either peripheral (CCK-B) receptors using homogenated rat pancreatic membranes as the receptor source or for central (CCK-B) receptors using bovine striatum as the receptor source.They were further evaluated for effects on food intake in rats after intraperitoneal (ip) injection.A number of the compounds reported are active in the CCK-A receptor binding assay although less potent than acetyl-CCK-7 and decrease food intake with comparable potency to acetyl-CCK-7.In a meal feeding model designed to assess appetite suppressant activity, acetyl-CCK-7 has an ED50 of 7 nmol/kg ip, while the ED50s of Ac-Phe(4-CH2CO2H)-Met-Gly-Trp-Met-Asp-Phe-NH2 (28) and Ac-Phe-Met-Gly-Trp-Met-Asp-Phe-NH2 (34) were 9 and 11 nmol/kg ip, respectively.An analogue of 28 lacking the N-terminal acetamido group, 3-propanoyl-Met-Gly-Trp-Met-Asp-Phe-NH2 (50), was also active in the meal feeding assay with an ED50 of 3 nmol/kg ip.Its anorexic effect was blocked by simultaneous administration of the CCK-A receptor antagonist MK 329, indicating that the observed anorexic activity is mediated by CCK-A receptors.We conclude from this work that the requirement for a negative charge at the CCK-A receptor provided in the natural substrate by a sulfate group can be satisfied by organic acids.