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

• 456-55-3 1-trifluoromethoxybenzene 
• 108-86-1 bromobenzene 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 106-40-1 4-bromo-aniline 
• 807368-45-2 ethyl 2-( 4-bromophenoxy)-2,2-difluoroacetate 
• 106-41-2 4-bromo-phenol 
• 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 
• 1006904-72-8 silver(I) trifluoromethoxide 

Downstream Products

• 34367-36-7 (4-bromophenyl)[4-(trifluoromethoxy)phenyl]methanone 
• 123846-75-3 N-Pyridin-3-yl-N-(4-trifluoromethoxy-phenyl)-acetamide 
• 196811-90-2 2‐[4‐(trifluoromethoxy)phenyl]ethanol 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 252955-06-9 ethyl 3-oxo-3-[4-(trifluoromethoxy)phenyl]propanoate 
• 139301-27-2 4-trifluoromethoxyphenylboronic acid 
• 659-28-9 p-trifluoromethoxybenzaldehyde 
• 133937-72-1 trifluoromethoxy-4-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-benzene 
• 169609-59-0 N-(4-propoxyphenylmethyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine 

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.

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.

Visible-Light Photoredox-Catalyzed and Copper-Promoted Trifluoromethoxylation of Arenediazonium Tetrafluoroborates

We report the development of photoredox-catalyzed and copper-promoted trifluoromethoxylation of arenediazonium tetrafluoroborates, with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. This new method takes advantage of visible-light photoredox catalysis to generate the aryl radical under mild conditions, combined with copper-promoted selective trifluoromethoxylation. The reaction is scalable, tolerates a wide range of functional groups, and proceeds regioselectively under mild reaction conditions. Furthermore, mechanistic studies suggested that a Cs[Cu(OCF3)2] intermediate might be generated during the reaction.