2252-44-0

Basic information

• Product Name: 3-(Trifluoromethoxy)bromobenzene
• Synonyms: 3-Bromophenyl trifluoromethyl ether, 3-Bromo-alpha,alpha,alpha-trifluoroanisole;3-(trifluoromrthoxy)bromobenzene;Inter-bromo-trifluoromethoxy benzene;Anisole, m-bromo-alphaalphaalpha-trifluoro-;BUTTPARK 91\57-27;M-BROMO(TRIFLUOROMETHOXY)BENZENE;1-BROMO-3-(TRIFLUOROMETHOXY)BENZENE;3-(TRIFLUOROMETHOXY)BROMOBENZENE
• CAS NO: 2252-44-0
• Molecular Formula: C₇H₄BrF₃O
• Molecular Weight: 241.01
• Product Categories: alkyl bromide;Trifluoroanisole series;Fluorobenzene;Halides;Aromatic Ethers;Phenyls & Phenyl-Het;Miscellaneous;Phenyls & Phenyl-Het;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 2252-44-0.mol

Chemical Properties

• Boiling Point: 156-158 °C
• Flash Point: 145 °F
• Appearance: Clear very faintly yellow liquid
• Density: 1.62 g/mL at 25 °C(lit.)
• Vapor Pressure: 3mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1945938
• CAS DataBase Reference: 3-(Trifluoromethoxy)bromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Trifluoromethoxy)bromobenzene(2252-44-0)
• EPA Substance Registry System: 3-(Trifluoromethoxy)bromobenzene(2252-44-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2252-44-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-(Trifluoromethoxy)bromobenzene is used as a key intermediate in the preparation of 1,2-dehydro-3-(trifluoromethoxy)benzene, which is an essential compound for further chemical reactions and synthesis processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(Trifluoromethoxy)bromobenzene is utilized as a starting material for the synthesis of new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep [2,2′-bis(diphenylphosphino)-6,6′-ditrifluoromethoxy-1,1′-biphenyl]. This ligand plays a crucial role in the development of novel pharmaceutical compounds and catalysts for various applications.
Used in Material Science:
3-(Trifluoromethoxy)bromobenzene's unique chemical properties make it a valuable component in the development of new materials with specific electronic, optical, or mechanical properties. Its use in material science can lead to the creation of advanced materials for various industries, including electronics, aerospace, and automotive.

InChI:InChI=1/C7H4BrF3S/c8-5-2-1-3-6(4-5)12-7(9,10)11/h1-4H

Upstream product

• 591-20-8 3-Bromophenol 
• 461-82-5 4-(trifluoromethoxy)aniline 
• 175278-09-8 4-bromo-2-(trifluoromethoxy)aniline 
• 108-86-1 bromobenzene 
• 1006904-72-8 silver(I) trifluoromethoxide 
• 591-19-5 m-Bromoaniline 
• 64115-88-4 1-bromo-2-(trifluoromethoxy)benzene 
• 927-84-4 bis(trifluoromethyl)peroxide 

Downstream Products

• 705-44-2 m-methyl-α,α,α-trifluoromethoxybenzene 
• 642444-30-2 2-[3-(trifluoromethoxy)phenyl]ethanol 
• 1014-81-9 3-(trifluoromethoxy)benzoic acid 
• 179113-90-7 (3-(trifluoromethoxy)phenyl)boronic acid 
• 198206-33-6 1-iodo-3-(trifluoromethoxy)benzene 
• 52771-21-8 3-(trifluoromethoxy)benzaldehyde 
• 403646-46-8 3-bromo-6-(trifluoromethoxy)benzoic acid 
• 403646-58-2 8-(trifluoromethoxy)-1-naphthol 
• 866683-58-1 trimethyl-(3-trifluoromethoxyphenylethynyl)-silane 
• 197847-90-8 2-(3-Trifluoromethoxyphenyl)-5-methylpyridine 
• 936092-86-3 C₁₂H₉ClF₃N₃O 
• 54711-69-2 1-(3-trifluoromethoxyphenyl)piperazine 
• 1060691-36-2 1-bromo-2-iodo-3-trifluoromethoxy-benzene 
• 1047670-50-7 [5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]-(3-trifluoromethoxyphenyl)-methanone 

Relevant articles and documents

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison t

Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines

The base-catalyzed isomerization of simple aryl halides is presented and utilized to achieve the 4-selective etherification, hydroxylation and amination of 3-bromopyridines. Mechanistic studies support isomerization of 3-bromopyridines to 4-bromopyridines proceedsviapyridyne intermediates and that 4-substitution selectivity is driven by a facile aromatic substitution reaction. Useful features of a tandem aryl halide isomerization/selective interception approach to aromatic functionalization are demonstrated. Example benefits include the use of readily available and stable 3-bromopyridines in place of less available and stable 4-halogenated congeners and the ability to converge mixtures of 3- and 5-bromopyridines to a single 4-substituted product.

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF3 group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF3 as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF3 bonds.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C?H Trifluoromethoxylation

The trifluoromethoxy (OCF3) radical is of great importance in organic chemistry. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF3 radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermolecular C?H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF3 radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation.

Catalytic C?H Trifluoromethoxylation of Arenes and Heteroarenes

The intermolecular C?H trifluoromethoxylation of arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a novel trifluoromethoxylating reagent and redox-active catalysts for the direct (hetero)aryl C?H trifluoromethoxylation. Our approach is operationally simple, proceeds at room temperature, uses easy-to-handle reagents, requires only 0.03 mol % of redox-active catalysts, does not need specialized reaction apparatus, and tolerates a wide variety of functional groups and complex structures such as sugars and natural product derivatives. Importantly, both ground-state and photoexcited redox-active catalysts are effective. Detailed computational and experimental studies suggest a unique reaction pathway where photoexcitation of the trifluoromethoxylating reagent releases the OCF3 radical that is trapped by (hetero)arenes. The resulting cyclohexadienyl radicals are oxidized by redox-active catalysts and deprotonated to form the desired products of trifluoromethoxylation.

Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N?O Bond Redox Fragmentation

A simple trifluoromethoxylation method enables non-directed functionalization of C?H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, which triggers an N?O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.

PROCESS FOR THE PREPARATION OF 1-BROMO-3-TRIFLUOROMETHOXYBENZENE

The invention concerns a process for the preparation of 1-bromo-3- trifluoromethoxybenzene starting from 2- or 4-trifluoromethoxyaniline or a mixture of these compounds via a synthesis that provides excellent yields and surprising selectivity.

[Perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes and method of preparing same

The invention relates to [perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes characterized by the general formula STR1 where: RF = OCF3 OC2 F5, OC2 F4 OCF3, C2 F4 OCF3, C3 F7 and also to a method of preparing them. The method according to the invention consists in that fluorobromo[alkyl(alkoxy)]benzenes having the general formula STR2 where: RF = OCF3 OC2 F5, OC2 F4 OCF3, C2 F4 OCF3, C3 F7 are treated with magnesium taken in a 5 - 20 per cent excess with respect to the stoichiometric quantity in a solution of absolute diethyl ether or absolute tetrahydrofurane at a temperature of 8° - 60° C. The resulting fluorine-containing magnesiumbromo[alkyl(alkoxy)]benzenes are treated with three-functional silanes -- methyltrichlorosilane -- taken in a 100 - 500 per cent excess with respect to the stoichiometric quantity, or with methylchlorodiethoxysilane, taken in the stoichiometric quantity or in a 50 per cent excess with respect to the stoichiometric quantity, at a temperature of 18° - 60° C. In the case of methylchlorodiethoxysilane, the resultant product is fluorine-containing [alkyl(alkoxy)phenyl]methyldiethoxysilanes which are treated with acetyl chloride taken in a 25 - 50 per cent excess with respect to the stoichiometric quantity, at a temperature of 40° - 70° C, in the presence of ferric chloride as a catalyst. The proposed [perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes can be used for preparing organofluosilicon lubricants, greases, sealing counds, rubber mixtures having high resistance to heat, frost, petrol and oils, that can be used in various fields of technology. The described method can be used to obtain the proposed end products in yields as high as 96 per cent of theory.