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Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1-Bromo-4-(bromodifluoromethyl)benzene is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a wide range of bioactive compounds, contributing to the development of new drugs and pesticides.
Used in Dye and Optical Brightener Production:
1-Bromo-4-(bromodifluoromethyl)benzene also serves as a crucial component in the production of dyes and optical brighteners. Its chemical properties make it suitable for enhancing the color and brightness of various products, such as textiles, plastics, and paper.
Used in Organic Chemistry as a Reagent:
1-Bromo-4-(bromodifluoromethyl)benzene is employed as a reagent in a variety of organic chemistry reactions. Its ability to participate in different types of chemical transformations makes it a valuable tool for researchers and chemists in the field.
Used as a Precursor for Other Organic Compounds:
Due to its versatile structure, 1-Bromo-4-(bromodifluoromethyl)benzene is used as a precursor for the synthesis of other organic compounds. This allows for the creation of new materials and substances with potential applications in various industries.
Used in Industrial Applications:
1-Bromo-4-(bromodifluoromethyl)benzene has a broad range of industrial applications, including its use as a reagent and precursor in the synthesis of various products. Its versatility and chemical properties make it an important compound in the development of new technologies and materials.

Upstream product

• 51776-71-7 p-bromo-α,α-difluorotoluene 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 1004305-97-8 2-(4-bromophenyl)-2,2-difluoroacetic acid ethyl ester 
• 913574-93-3 2-(4-bromophenyl)-2,2-difluoroacetic acid 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 76092-29-0 1-bromo-4-(tribromomethyl)benzene 

Downstream Products

• 934753-13-6 {2-[(4-bromophenyl)(difluoro)methoxy]-5-fluorophenyl}methanol 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 182676-39-7 5-((4-bromophenyl)difluoromethoxy)-1,2,3-trifluorobenzene 

Relevant academic research and scientific papers

Synthesis of ArCF2X and [18F]Ar-CF3via Cleavage of the Trifluoromethylsulfonyl Group

A versatile synthesis of ArCF2X and [18F]Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F-, Cl-, Br-, and I-), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.

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.

Iron-Catalyzed Halogen Exchange of Trifluoromethyl Arenes**

The facile production of ArCF2X and ArCX3 from ArCF3 using catalytic iron(III)halides is reported, which constitutes the first iron-catalyzed halogen exchange for non-aromatic C?F bonds. Theoretical calculations suggest direct activation of C?F bonds by iron coordination. ArCX3 and ArCF2X products of the reaction are synthetically valuable due to their diversification potential. In particular, chloro- and bromodifluoromethyl arenes (ArCF2Cl, ArCF2Br respectively) provide access to a myriad of difluoromethyl arene derivatives (ArCF2R). To optimize for mono-halogen exchange, a statistical method called Design of Experiments was used. Optimized parameters were successfully applied to electron rich and electron deficient aromatic substrates, and to the late stage diversification of flufenoxuron, a commercial insecticide. These methods are highly practical, being run at convenient temperatures and using inexpensive common reagents.

Frustrated Lewis-Pair-Meditated Selective Single Fluoride Substitution in Trifluoromethyl Groups

Single fluoride substitution in trifluoromethylarenes is an ongoing synthetic challenge that often leads to "over-reaction", where multiple fluorides are replaced. Development of this reaction would allow simple access to a vast range of difluoromethyl derivatives of current interest to pharmaceutical, agrochemistry, and materials sciences. Using a catalytic frustrated Lewis pair approach, we have developed a generic protocol that allows a single substitution of one fluoride in trifluoromethyl groups with neutral phosphine and pyridine bases. The resulting phosphonium and pyridinium salts can be further functionalized via nucleophilic substitution, photoredox coupling, and electrophilic transfer reactions allowing the generation of a vast array of difluoromethyl products.

Synthesis of trifluoromethyl moieties by late-stage copper (I) mediated nucleophilic fluorination

The nucleophilic fluorination of bromodifluoromethyl derivatives mediated by the complex (PPh3)3CuF is described. Under the reaction conditions, different trifluoroacetates, trifluoroketones, trifluoroarenes and trifluoroacetamides were obtained in good yields.

Method of manufacturing hydroxybenzenesulfonic deriv. Halomethylation

PROBLEM TO BE SOLVED: To provide a method for producing a halomethylbenzene derivative by halogenating a methylbenzene derivative at the benzyl position, which is industrially achievable. SOLUTION: In the method for producing a halomethylbenzene derivative represented by formula (2) (wherein R1-R5are each independently a hydrogen atom, tert-butyl, phenyl or the like; X, Y and Z are each independently a halogen atom; p and q are each independently 0, 1 or 2; z is 1, 2 or 3 and p+q+z is 1, 2 or 3) by halogenating a methylbenzene derivative by light or heat, halogenation is carried out in a chain fluorine-containing hydrocarbon or cyclic fluorine-containing hydrocarbon. COPYRIGHT: (C)2011,JPOandINPIT

Heterocyclic compounds with carboxyl isostere groups and their use for the treatment of cardiovascular diseases

The present application relates to novel heterocyclic compounds, processes for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for producing medicaments for the treatment and/or prophylaxis of diseases, especia