913574-93-3

Basic information

• Product Name: 2-(4-bromophenyl)-2,2-difluoroacetic acid
• Synonyms: 2-(4-bromophenyl)-2,2-difluoroacetic acid;4-Bromo-alpha,alpha-difluorobenzeneacetic acid;Benzeneacetic acid, 4-bromo-α,α-difluoro-;(4-Bromophenyl)(difluoro)acetic acid
• CAS NO: 913574-93-3
• Molecular Formula: C₈H₅BrF₂O₂
• Molecular Weight: 251.0249064
• Mol File: 913574-93-3.mol

Chemical Properties

• Boiling Point: 323℃
• Flash Point: 149℃
• Appearance: /
• Density: 1.733
• CAS DataBase Reference: 2-(4-bromophenyl)-2,2-difluoroacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromophenyl)-2,2-difluoroacetic acid(913574-93-3)
• EPA Substance Registry System: 2-(4-bromophenyl)-2,2-difluoroacetic acid(913574-93-3)

Safety Data

• Hazardous Substances Data: 913574-93-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(4-bromophenyl)-2,2-difluoroacetic acid is utilized as a key intermediate in organic synthesis for the production of various organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of complex molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(4-bromophenyl)-2,2-difluoroacetic acid is employed as a building block for the development of new drugs. Its chemical properties and potential interactions with biological systems make it a promising candidate for the creation of innovative therapeutic agents with diverse applications.
Used in Medicinal Chemistry:
2-(4-bromophenyl)-2,2-difluoroacetic acid is also used in medicinal chemistry studies to explore its potential interactions with biological targets. Its unique structure allows for the investigation of its binding affinity and selectivity towards specific proteins or enzymes, which can lead to the discovery of new drug candidates with improved efficacy and selectivity.
Used in Bioorganic Chemistry:
Furthermore, 2-(4-bromophenyl)-2,2-difluoroacetic acid is a subject of interest in bioorganic chemistry, where researchers study its interactions with biological systems. This knowledge can contribute to the understanding of its potential applications in drug design and the development of novel bioactive compounds with specific biological activities.

Upstream product

• 1022155-94-7 methyl 2-(4-bromophenyl)-2,2-difluoroacetate 
• 1004305-97-8 2-(4-bromophenyl)-2,2-difluoroacetic acid ethyl ester 
• 589-87-7 1,4-bromoiodobenzene 
• 667-27-6 Ethyl bromodifluoroacetate 
• 20201-26-7 ethyl 4-bromophenylglyoxylate 
• 108-86-1 bromobenzene 

Downstream Products

• 51776-71-7 p-bromo-α,α-difluorotoluene 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 1022155-94-7 methyl 2-(4-bromophenyl)-2,2-difluoroacetate 
• 2358-32-9 1-bromo-4-(bromodifluoromethyl)benzene 

Relevant articles and documents

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.

Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination

Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational circular dichroism (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a syn-β-fluoride elimination pathway rather than an anti-elimination pathway. The effects of the C1-symmetric Josiphos-derived ligand on reactivity and enantioselectivity were investigated. Not only does this report showcase that alkenyl copper species (like their alkyl counterparts) can undergo β-fluoride elimination, but this elimination can be achieved in an enantioselective fashion.

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

Synthetic method of aromatic ring group or aromatic heterocyclic tetrazole

The synthetic method comprises the following steps: (1) reacting 1.0 eq of ArI or HArI with 1.2 eq of ethyl 2, 2-difluoroacetate in the presence of DMSO as a solvent and 4.0 eq of Cu under the protection of nitrogen at 30 DEG C and 50 DEG C, and purifying to obtain a first intermediate compound; (2) dissolving 1.0 eq of the first intermediate compound in a mixed solvent of THF and water, adding 2.0 eq of LiOH, reacting at room temperature for 2 hours, spin-drying the solvent, adding HCl until the pH value is equal to 3, and filtering to obtain a second intermediate compound; and (3) reacting 1.0 eq of the second intermediate compound with 2.0 eq of diphenyl azide phosphate in the presence of 2.5 eq of triethylamine by taking tert-butyl alcohol as a solvent to generate aromatic ring group or aromatic heterocyclic tetrazole. The invention provides a novel synthetic method of aromatic ring group or aromatic heterocyclic tetrazole, wherein a target compound can be more conveniently obtained, and reagents participating in the reaction are low in toxicity, mild in reaction condition, simple and safe in aftertreatment, good in product quality and suitable for large-scale production.

Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids

A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.

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.

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.

Method of manufacturing arom. defluoromethyl compd.

PROBLEM TO BE SOLVED: To provide a method for easily producing an aromatic compound having a difluoromethyl group in high yield while using a reagent having low toxicity. SOLUTION: The method for producing the aromatic difluoromethyl compound includes reacting an aromatic difluoroacetic acid in the presence of a metal halide (especially potassium fluoride). COPYRIGHT: (C)2011,JPOandINPIT

Catalytic decarboxylative fluorination for the synthesis of Tri- and difluoromethyl arenes

Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [18F]labeling is demonstrated using [ 18F]Selectfluor bis(triflate), a reagent affording [ 18F]tri- and [18F]difluoromethylarenes not within reach with [18F]F2.

METHOD FOR PRODUCING AROMATIC DIFLUOROACETIC ACID ESTER

Disclosed is a method for producing a compound having a difluoromethylene group at an even lower cost and with excellent yield. The production method of the present invention is a method for producing an aromatic difluoroacetic acid ester, which comprises reacting an iodobenzene containing an electro attracting group and an α-silyl difluoroacetic acid ester in the presence of a metal halide.