402-23-3

Basic information

• Product Name: 3-(Trifluoromethyl)benzyl bromide
• Synonyms: 3-(TrifluoroMethyl)broMide;3-(Bromomethyl)benzotrifluoride alpha-Bromo-alpha',alpha',alpha'-trifluoro-m-xylene;3-(Bromomethyl)benzotrifluoride, 1-(Bromomethyl)-3-(trifluoromethyl)benzene;ALPHA'-BROMO-ALPHA,ALPHA,ALPHA-TRIFLUORO-M-XYLENE;ALPHA-BROMO-ALPHA',ALPHA',ALPHA'-TRIFLUORO-M-XYLENE;A'-BROMO-A,A,A-TRIFLUORO-M-XYLENE;3-(TRIFLUOROMETHYL)BENZYL BROMIDE;3-(BROMOMETHYL)BENZOTRIFLUORIDE
• CAS NO: 402-23-3
• Molecular Formula: C₈H₆BrF₃
• Molecular Weight: 239.03
• EINECS: 206-938-9
• Product Categories: NULL;Halogenated Heterocycles ,Pyrimidines;Fluoro-contained benzyl bromide series;Aromatic Halides (substituted);Miscellaneous;Benzenes;Benzyl;Aromatics;Miscellaneous Reagents
• Mol File: 402-23-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 69 °C4 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.565 g/mL at 25 °C(lit.)
• Vapor Pressure: 22.1mmHg at 25°C
• Refractive Index: n20/D 1.492(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive: Lachrymatory
• BRN: 743243
• CAS DataBase Reference: 3-(Trifluoromethyl)benzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Trifluoromethyl)benzyl bromide(402-23-3)
• EPA Substance Registry System: 3-(Trifluoromethyl)benzyl bromide(402-23-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 402-23-3(Hazardous Substances Data)

Usage

Description

3-(Trifluoromethyl)benzyl bromide is an organic compound with the chemical formula C8H6BrF3. It is a colorless to light yellow liquid at room temperature and is known for its reactivity in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
3-(Trifluoromethyl)benzyl bromide is used as a synthetic intermediate for the preparation of 1-benzylazetidine-3-carboxylic acid derivatives, which serve as agonists and antagonists of the S1P5 receptor. These compounds have potential applications in the treatment of various diseases and conditions, including autoimmune disorders and cancer.
Used in Agrochemical Industry:
3-(Trifluoromethyl)benzyl bromide has been utilized in the preparation of flocoumafen, a compound with potential applications in the development of novel agrochemicals for pest control and crop protection.
Used in Chemical Synthesis:
Due to its reactivity, 3-(Trifluoromethyl)benzyl bromide can be employed as a building block in the synthesis of various organic compounds, particularly those containing the trifluoromethyl group, which is known for its unique chemical and biological properties. This makes it a valuable reagent in the fields of medicinal chemistry, materials science, and specialty chemicals.

InChI:InChI=1/C8H4F6/c9-7(10,11)5-2-1-3-6(4-5)8(12,13)14/h1-4H

Upstream product

• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 401-79-6 1-methyl-3-trifluoromethyl-benzene 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 

Downstream Products

• 788-03-4 N-(3-Trifluormethyl-benzyloxy)-carbamidsaeure-ethylester 
• 2729-72-8 N-(2-Trifluormethyl-benzyl)-N-(3-trifluormethyl-benzyloxy)-carbamidsaeure-ethylester 
• 2338-76-3 3-trifluoromethylphenylacetonitrile 
• 90390-07-1 N-methyl-1-(3-(trifluoromethyl)phenyl)methanamine 
• 130828-94-3 [1-{[1-Phenyl-meth-(E)-ylidene]-amino}-2-(3-trifluoromethyl-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 103119-48-8 1-[3-(3-Trifluoromethyl-benzyloxy)-phenyl]-hexan-1-ol 
• 145243-33-0 2-(Benzhydrylidene-amino)-3-(3-trifluoromethyl-phenyl)-propionic acid methyl ester 
• 104586-84-7 3,4-Dihydro-9-(3-trifluoromethylbenzylamino)acridin-1(2H)-one 
• 104705-70-6 9-(3-Trifluoromethyl-benzylsulfanyl)-1,2,3,4-tetrahydro-acridine 
• 119984-56-4 1-(3-trifluoromethyl)benzyl-5-n-octyloxy-pyrrolidin-2-one 
• 3029-30-9 naphthalene-1,4-dicarbonitrile 
• 401-79-6 1-methyl-3-trifluoromethyl-benzene 
• 19519-94-9 3-Trifluormethyl-benzylfluorid 
• 1027075-63-3 (S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 3-trifluoromethyl-benzyl ester 

Relevant articles and documents

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions

The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.

Aryl sulfonamide and sulfonyl compounds as modulators of PPAR and methods of treating metabolic disorders

Aryl sulfonamide and sulfonyl compounds as modulators of peroxisome proliferator activated receptors, pharmaceutical compositions comprising the same, and methods of treating disease using the same are disclosed.