407-14-7

Basic information

• Product Name: 1-Bromo-4-(trifluoromethoxy)benzene
• Synonyms: 4-BROMO-ALPHA,ALPHA,ALPHA-TRIFLUOROANISOLE;4-BROMO(TRIFLUOROMETHOXY)BENZENE;4-(TRIFLUOROMETHOXY)BROMOBENZENE;1-BROMO-4-(TRIFLUOROMETHOXY)BENZENE;TIMTEC-BB SBB006606;P-TRIFLUOROMETHOXY BROMOBENZENE;P-BROMOTRIFLUOROMETHOXYBENZENE;Benzene, 1-bromo-4-(trifluoromethoxy)-
• CAS NO: 407-14-7
• Molecular Formula: C₇H₄BrF₃O
• Molecular Weight: 241.01
• EINECS: 206-979-2
• Product Categories: Trifluoroanisole series;Trifluoromethoxybenzene Series;Fluorobenzene;Aromatic Halides (substituted);Miscellaneous;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Fluorine Compounds;Building Blocks for Liquid Crystals;Chalcones, etc. (Building Blocks for Liquid Crystals);Functional Materials;Pharmaceutical Intermediate;Ethers;Organic Building Blocks;Oxygen Compounds;alkyl bromide
• Mol File: 407-14-7.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 80 °C50 mm Hg(lit.)
• Flash Point: 154 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.622 g/mL at 25 °C(lit.)
• Vapor Pressure: 6mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 11.7mg/l
• BRN: 2046332
• CAS DataBase Reference: 1-Bromo-4-(trifluoromethoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-(trifluoromethoxy)benzene(407-14-7)
• EPA Substance Registry System: 1-Bromo-4-(trifluoromethoxy)benzene(407-14-7)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-36/37/38-43-51/53
• Safety Statements: 26-36/37-61-37/39-36
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 407-14-7(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO YELLOW LIQUID

Uses

1-Bromo-4-(trifluoromethoxy)benzene was used in the synthesis of 4-{[4-[(2-ethylhexyloxy)-6-(4-morpholinylmethyl)-4-trifluoromethyl][1,1-biphenyl]-3-yl]methyl}morpholine.

Synthesis Reference(s)

Journal of the American Chemical Society, 109, p. 3708, 1987 DOI: 10.1021/ja00246a030

General Description

1-Bromo-4-(trifluoromethoxy)benzene on treatment with lithium diisopropylamide (LIDA) at -100°C gives 5-bromo-2-(trifluoromethoxy)phenyllithium and at -75°C it eliminates lithium bromide, thus generating 1,2-dehydro-4-(trifluoromethoxy)benzene.

InChI:InChI:1S/C7H4BrF3O/c8-5-1-3-6(4-2-5)12-7(9,10)11/h1-4H

Upstream product

• 106-41-2 4-bromo-phenol 
• 456-55-3 1-trifluoromethoxybenzene 
• 108-86-1 bromobenzene 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 106-40-1 4-bromo-aniline 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 1006904-72-8 silver(I) trifluoromethoxide 
• 807368-45-2 ethyl 2-( 4-bromophenoxy)-2,2-difluoroacetate 
• 17151-49-4 (4-bromophenyl)tri-n-butylstannane 
• 96898-10-1 tris(dimethylamino)sulfonium trifluoromethoxide 
• 143582-87-0 O-4-bromophenyl S-methyl dithiocarbonate 
• 353-50-4 Carbonyl fluoride 

Downstream Products

• 34367-38-9 4-Trifluormethoxy-3',5'-dichlorbenzophenon 
• 34328-45-5 4-Trifluormethoxy-3'-trifluormethyl-4'-brombenzophenon 
• 34367-36-7 (4-bromophenyl)[4-(trifluoromethoxy)phenyl]methanone 
• 283168-40-1 3-tetrahydropyran-2-yloxy-2,2,4,4-tetramethyl-1-(4-trifluoromethoxyphenyl)cyclobutanol 
• 326474-05-9 1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyloxy)benzene 
• 103962-05-6 1-iodo-4-(trifluoromethoxy)benzene 
• 139301-27-2 4-trifluoromethoxyphenylboronic acid 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 252955-06-9 ethyl 3-oxo-3-[4-(trifluoromethoxy)phenyl]propanoate 
• 706-27-4 p-methyl-α,α,α-trifluoromethoxybenzene 
• 305794-52-9 4-[hydroxy-(4-trifluoromethoxy-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester 
• 173025-79-1 4-(4'-trifluoromethoxy phenyl)-phenol 
• 220616-04-6 (R)-1-Benzyloxy-3-(4'-trifluoromethoxy-biphenyl-4-yloxy)-propan-2-ol 
• 220616-11-5 3-((2S)-2-(N-hydroxyamino)-3-((4'-(trifluoromethoxy)(1,1'-biphenyl)-4-yl)oxy)propyl)-5,5-dimethyl-2,4-imidazolidinedione 

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.

Sequential Xanthalation and O-Trifluoromethylation of Phenols: A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers

Molecules containing trifluoromethoxyaryl groups are of interest in pharmaceutical, agrochemical, and materials science research, due to their unique physical and electronic properties. Many of the known methods to synthesize aryl trifluoromethyl ethers require harsh reagents and highly controlled reaction conditions and rarely occur when heteroaromatic units are present. The two-step O-trifluoromethylation of phenols via aryl xanthates is one such method that suffers from these drawbacks. Herein, we report a method for the synthesis of aryl trifluoromethyl ethers from phenols by the facile conversion of the phenol to the corresponding aryl and heteroaryl xanthates with newly synthesized imidazolium methylthiocarbonothioyl salts and conversion of these xanthates to the trifluoromethyl ethers under mild reaction conditions.

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.