32247-96-4

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)benzyl bromide
• Synonyms: 3,5-Bis(trifluoromethyl)benzyl bromide, 97+%;1,3-Bis(trifluoromethyl)-5-(bromomethyl)benzene;3,5-Bis(trifluoromethyl)benzylbromiode;5-Bis(trifluoroMethyl)benzyl broMide;3,5-Bis(trifluoremethyl)benzylbromide;{[3,5-bis(trifluoroMethyl)phenyl]Methyl}broManuide;3,5-Bis(trifluoroMethyl)benzyl broMide, 97% 1GR;Benzene,1-(broMoMethyl)-3,5-bis(trifluoroMethyl)-
• CAS NO: 32247-96-4
• Molecular Formula: C₉H₅BrF₆
• Molecular Weight: 307.03
• EINECS: 250-971-1
• Product Categories: Fluorides;Aromatic Halides (substituted)
• Mol File: 32247-96-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 18°C
• Boiling Point: 136-140°C 14mm
• Flash Point: 79 °F
• Appearance: Clear colorless to yellow-brown/Liquid
• Density: 1.675 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.34mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Storage Temp.: Flammables area
• Solubility: Difficult to mix.
• Sensitive: Lachrymatory
• BRN: 656506
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)benzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)benzyl bromide(32247-96-4)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)benzyl bromide(32247-96-4)

Safety Data

• Hazard Codes: C,F
• Statements: 10-34
• Safety Statements: 26-36/37/39-45-25-16
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 32247-96-4(Hazardous Substances Data)

Usage

Description

3,5-Bis(trifluoromethyl)benzyl bromide is an organic compound characterized by the presence of two trifluoromethyl groups attached to a benzyl bromide moiety. It exhibits a range of colors from white to yellow, orange, or even as a clear liquid, depending on its purity and concentration.

Uses

Used in Analytical Chemistry:
3,5-Bis(trifluoromethyl)benzyl bromide is used as a derivatization reagent for the detection of uracil in DNA. This application is particularly useful in gas chromatography (GC) and negative chemical ionization mass spectrometry, where it aids in the identification and quantification of uracil, a key component of DNA.
Used in Pharmaceutical Industry:
In the enantioselective synthesis of non-peptidic neurokinin NK1 receptor antagonists, 3,5-Bis(trifluoromethyl)benzyl bromide serves as a crucial intermediate. Its unique structural features and reactivity make it an effective component in the development of these antagonists, which have potential applications in treating various disorders related to the neurokinin NK1 receptor.

Synthesis

Synthesis of 3, 5-bis (trifluoromethyl)-benzyl bromide:In a 4-neck flask with capacity 1000 ml equipped with mechanical agitator, thermometer, bubble condenser and 100 ml loading funnel, 262.2 g of the product of Example 1 (ii) at 92. 8% (0. 988 moles), 550,2 g HBr 48% (3.2645 moles) are loaded; this is heated at 50°C so as to melt the alcohol, then one starts to dose 113 g of concentrated His04 (1.153 moles). Pouring is accomplished in 30 minutes, noting an increase of the internal temperature. This is heated to 100-105°C and left to react for 8 hours. The reaction is completed by reflux heating for per 1.5 hours. the mixture is left to settle and the phases are separated; the solvents are removed from the organic phase and the product in the title is obtained with a yield of 99.1 %.

InChI:InChI=1/C9H5BrF6/c10-4-5-1-6(8(11,12)13)3-7(2-5)9(14,15)16/h1-3H,4H2

Upstream product

• 32707-89-4 3,5-bis(trifluoromethyl)benzenemethanol 

Downstream Products

• 132130-91-7 2-(3,5-Bis-trifluoromethyl-benzyloxy)-1,1,2,2-tetrafluoro-ethanesulfonyl fluoride 
• 754-41-6 2-(fluorosulfonyl)tetrafluoropropionyl fluoride 
• 132130-92-8 1-(3,5-Bis-trifluoromethyl-benzyloxy)-1,1,2,3,3,3-hexafluoro-propane-2-sulfonyl fluoride 
• 169673-06-7 3,5-bis(trifluoromethyl)benzyl N-(tert-butoxycarbonyl)-L-tryptophanate 
• 1060667-52-8 3-Benzo[b]thiophen-3-yl-2-tert-butoxycarbonylamino-propionic acid 3,5-bis-trifluoromethyl-benzyl ester 
• 160376-91-0 1-tert-butoxycarbonyl-4-phenyl-4[[(3,5-bis-trifluoromethyl)]benzyloxymethyl]piperidine 
• 125138-12-7 diethyl 3,5-bis(trifluoromethyl)benzyl phosphonate 
• 159706-37-3 (2R,3S)-4-Benzyl-2-(3,5-bis-trifluoromethyl-benzyloxy)-3-phenyl-morpholine 

Relevant articles and documents

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization

A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

N-acylamino benzyl ether derivatives

This invention relates to N-acylamino aryl derivatives of the formula 1where R1, R21, R22, R23, R3, R4, R5 R6, R7, R8, R, and n are as defined herein and where X is —CHRO, —OCHR—, —CH2S—, —SCH2—, —CH2CH2—, —CH=CH— or —C≡C—. The compounds of the invention are selective monoamine oxidase B inhibitors, and they are therefore useful in the treatment of diseases mediated by monoamine oxidase B, for example, for the treatment of Alzheimer's disease or senile dementia.

2-OXABICYCLO(2,2,1)HEPTANE DERIVATIVES AND PHARMACEUTICAL

The invention relates to 2-oxabicyclo[2.2.1]heptane derivatives of formula I (I) as well as their enantiomers, in which, e.g., A means -(CH2)n-, (E)- or (Z)-CH=CH-, -C 3BOND C, -O- or -S-, B means hydrogen, C1-C10 alkyl, -OR2, halogen, -C 3BOND N, -N3, -COOR3, R1 means oxygen or a -CH2 group, Z means -(CH2)p-, (E)-CH=CH-, -C 3BOND C-, W means a direct bond, a free or functionally modified hydroxymethylene group or a free or functionally modified in which the OH group can be respectively in alpha- or beta-position, D means a direct bond, a saturated alkylene group with 1-5 C atoms, a branched saturated or a straight-chain of branched unsaturated alkylene group with 2-5 C atoms, E means a direct bond, -C 3BOND C- or -CH=CR7, R8 means hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, optionally substituted C6-C12 aryl or a 5- or 6-member heterocyclic radical, and if R5 means hydrogen, their salts with physiologically compatible bases, as well as the alpha-, beta- or gamma-cyclodextrin clathrates, as well as the compounds of formula I encapsulated with liposomes, process for their production and the pharmaceutical agents containing these compounds. The compounds are thromboxane antagonists