155820-88-5

Basic information

• Product Name: 1-Bromo-4-(2,2,2-trifluoroethyl)benzene
• Synonyms: 1-Bromo-4-(2,2,2-trifluoroethyl)benzene;1-Bromo-4-(2,2,2-trifluoroethyl)
• CAS NO: 155820-88-5
• Molecular Formula: C₈H₆BrF₃
• Molecular Weight: 239.04
• Mol File: 155820-88-5.mol

Chemical Properties

• Melting Point: 54-57°C
• Boiling Point: 190.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.543±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-Bromo-4-(2,2,2-trifluoroethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-(2,2,2-trifluoroethyl)benzene(155820-88-5)
• EPA Substance Registry System: 1-Bromo-4-(2,2,2-trifluoroethyl)benzene(155820-88-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 155820-88-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-bromo-4-(2,2,2-trifluoroethyl)benzene is used as an intermediate in the synthesis of various pharmaceuticals for its ability to introduce specific functionalities into organic molecules, aiding in the development of new medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 1-bromo-4-(2,2,2-trifluoroethyl)benzene is utilized as a precursor in the creation of compounds that can be used in the development of pesticides and other agricultural chemicals, enhancing crop protection and yield.
Used in Organic Synthesis Research:
As a research chemical, 1-bromo-4-(2,2,2-trifluoroethyl)benzene is employed in organic synthesis to explore new reaction pathways and mechanisms, contributing to the advancement of chemical knowledge and the creation of novel compounds.
Used in Specialty Chemical Product Manufacturing:
1-bromo-4-(2,2,2-trifluoroethyl)benzene is also used in the production of specialty chemical products, where its unique structure allows for the creation of materials with specific properties tailored for various industrial applications.

InChI:InChI=1S/C8H6BrF3/c9-7-3-1-6(2-4-7)5-8(10,11)12/h1-4H,5H2

Upstream product

• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1895006-01-5 dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate 
• 887144-94-7 Togni's reagent II 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 5467-74-3 4-Bromophenylboronic acid 
• 373-88-6 2,2,2-trifluroethylamine hydrochloride 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 129946-88-9 Umemoto's reagent 
• 873-75-6 4-bromobenzenemethanol 
• 84750-93-6 1,1-difluoro-2-(4-bromophenyl)ethene 
• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 

Downstream Products

• 1198117-44-0 3-oxo-2-(2-(pyridin-2-yl)ethyl)-N-(4-(2,2,2-trifluoroethyl)benzyl)isoindoline-1-carboxamide 
• 1176282-86-2 4-(2,2,2-trifluoroethyl)benzoic acid 
• 1310949-87-1 4,4,5,5-tetramethyl-2-[4-(2,2,2-trifluoroethyl)phenyl]-1,3,2-dioxaborolane 
• 1256841-40-3 Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate 

Relevant articles and documents

Deoxofluorination of Aliphatic Carboxylic Acids: A Route to Trifluoromethyl-Substituted Derivatives

A practical method for the synthesis of functionalized aliphatic trifluoromethyl-substituted derivatives from aliphatic acids is developed. The transformation proceeds with sulfur tetrafluoride in the presence of water as a key additive. Compared to previous methods, the reaction gives products with full retention of stereo- and absolute configuration of chiral centers.

Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes

Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free.

Copper-Catalyzed Trifluoromethylation of Alkyl Bromides

Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.

Synthesis of trifluoromethylated compounds from alcohols via alkoxydiphenylphosphines

The transformation of hydroxyl group in benzyl or allyl alcohols to trifluoromethyl was achieved via the reaction of the corresponding alkyloxydiphenylphosphine and CuCF3, generated in situ from methyl fluorosulfonyldifluoroacetate and CuI, under mild conditions. A plausible mechanism was proposed on the basis of experimental results.

Switchable 2,2,2-trifluoroethylation and gem-difluorovinylation of organoboronic acids with 2,2,2-trifluorodiazoethane

The transition-metal-free 2,2,2-trifluoroethylation and gem-difluorovinylation of arylboronic acids were developed. By employing different reaction conditions, these transformations provide both (2,2,2-trifluoroethyl)arenes and gem-difluorovinylarenes fro

Copper-mediated deoxygenative trifluoromethylation of benzylic xanthates: Generation of a C-CF3 bond from an O-based electrophile

The conversion of an alcohol-based functional group, into a trifluoromethyl analogue is a desirable transformation. However, few methods are capable of converting O-based electrophiles into trifluoromethanes. The copper-mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF3 to form C-CF3 bonds is described. The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the C-CF3 bond forms by reaction of the substrate with in situ generated CuCF3 and CuOTf. Further evidence suggests that the reaction could proceed via a radical cation intermediate. Highly compatible and useful: The copper-mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF3 to form C-CF3 bonds is described (see scheme). The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the C-CF3 bond forms by reaction of the substrate with in situ generated CuCF3 and CuOTf. Copyright

SUBSTITUTED PIPERIDINES

The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and tumour disorders.

SUBSTITUTED PIPERIDINES

The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular diseases and tumour diseases.

Nucleophilic (phenylsulfonyl)difluoromethylation of alkyl halides using PhSO2CF2SiMe3: Preparation of gem-difluoroalkenes and trifluoromethyl compounds

Nucleophilic (phenylsulfonyl)difluoromethylation of both alkyl iodides and bromides was successfully accomplished by using CsF/15-crown-5 as an initiating system in DME, and the amount of 15-crown-5 was found to be critical to the yield of the product. The prepared (phenylsulfonyl)difluoromethylated alkanes were converted into gem-difluoroalkenes by a base-mediated 1,2-elimination reaction, and the latter species could be further transformed into trifluoromethyl compounds in the presence of KF/18-crown-6 or TBAF.

Novel ATP-competitive kinesin spindle protein inhibitors

Kinesin spindle protein (KSP), an ATPase responsible for spindle pole separation during mitosis that is present only in proliferating cells, has become a novel and attractive anticancer target with potential for reduced side effects compared to currently available therapies. We report herein the discovery of the first known ATP-competitive inhibitors of KSP, which display a unique activity profile as compared to the known loop 5 (L5) allosteric KSP inhibitors that are currently under clinical evaluation. Optimization of this series led to the identification of biphenyl sulfamide 20, a potent KSP inhibitor with in vitro antiproliferative activity against human cells with either wild-type KSP (HCT116) or mutant KSP (HCT116 D 130V). In a murine xenograft model with HCT116 D130V tumors, 20 showed significant antitumor activity following intraperitoneal dosing, providing in vivo proof-of-principle of the efficacy of an ATP-competitive KSP inhibitor versus tumors that are resistant to the other known KSP inhibitors.