402-49-3

Basic information

• Product Name: 4-(TRIFLUOROMETHYL)BENZYL BROMIDE
• Synonyms: TIMTEC-BB SBB006698;P-(TRIFLUOROMETHYL)BENZYL BROMIDE;1-(BROMOMETHYL)-4-(TRIFLUOROMETHYL)BENZENE;ALPHA'-BROMO-ALPHA,ALPHA,ALPHA-TRIFLUORO-P-XYLENE;ALPHA-BROMO-ALPHA',ALPHA',ALPHA'-TRIFLUORO-P-XYLENE;4-(TRIFLUOROMETHYL)BENZYL BROMIDE;4-(BROMOMETHYL)BENZOTRIFLUORIDE;Benzene, 1-(bromomethyl)-4-(trifluoromethyl)-
• CAS NO: 402-49-3
• Molecular Formula: C₈H₆BrF₃
• Molecular Weight: 239.03
• EINECS: 206-947-8
• Product Categories: Fluoro-contained benzyl bromide series;Miscellaneous;Benzyl
• Mol File: 402-49-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 29-33 °C(lit.)
• Boiling Point: 65-69 °C5 mm Hg(lit.)
• Flash Point: 192 °F
• Appearance: White to light yellow/Crystalline Low Melting Solid
• Density: 1.546 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.85mmHg at 25°C
• Refractive Index: n20/D 1.484(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility: Insoluble in water.
• Sensitive: Lachrymatory
• BRN: 638980
• CAS DataBase Reference: 4-(TRIFLUOROMETHYL)BENZYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHYL)BENZYL BROMIDE(402-49-3)
• EPA Substance Registry System: 4-(TRIFLUOROMETHYL)BENZYL BROMIDE(402-49-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 8-10-19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 402-49-3(Hazardous Substances Data)

Usage

Description

4-(Trifluoromethyl)benzyl Bromide is an organic compound characterized by the presence of a trifluoromethyl group attached to a benzyl bromide moiety. It is a valuable building block in the synthesis of various pharmaceutical compounds due to its unique structural features and reactivity.

Uses

Used in Pharmaceutical Industry:
4-(Trifluoromethyl)benzyl Bromide is used as a building block for the synthesis of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles, which exhibit antiviral activities. These compounds have potential applications in the development of new antiviral drugs to combat viral infections.
Used in Antiviral Drug Development:
4-(Trifluoromethyl)benzyl Bromide is used as a key intermediate in the preparation of 2-[(4-diarylmethoxy)phenyl]benzimidazoles. These compounds have been identified as potent inhibitors of the hepatitis C virus NS5B polymerase, making them valuable in the development of new treatments for hepatitis C.
Used in Medicine:
4-(Trifluoromethyl)benzyl bromide can be utilized to produce p-trifluoromethylbenzyl phenyl sulfide, a compound with potential applications in the medical field. The specific use of p-trifluoromethylbenzyl phenyl sulfide is not detailed in the provided materials, but it may have therapeutic properties or serve as a precursor to other medicinal compounds.
General Description:
The vibrational characteristics of 4-(trifluoromethyl)benzylbromide have been investigated, providing insights into its molecular structure and properties. This information can be useful for understanding its reactivity and potential applications in various chemical and pharmaceutical processes.

InChI:InChI=1/C9H7F3/c1-2-7-3-5-8(6-4-7)9(10,11)12/h2-6H,1H2

Upstream product

• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 6140-17-6 4-methylbenzotrifluoride 
• 774197-61-4 3-(p-trifluoromethylbenzyloxy)-3-bromoaziridine 
• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 77152-08-0 trifluoromethylcopper(I) 
• 100-39-0 benzyl bromide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Downstream Products

• 194222-97-4 (4-trifluoromethylphenyl)methyl trifluoromethyl sulfone 
• 287974-84-9 3-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-3,4-dihydro-2H-naphthalen-1-one 
• 136131-36-7 3-<(4-(trifluoromethyl)phenyl)methyl>furan 
• 99578-68-4 diethyl (4-(trifluoromethyl)benzyl)phosphonate 
• 79128-87-3 N-(4'-trifluoromethylbenzyl)-4-trifluoromethylaniline 

Relevant articles and documents

REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION

Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

Halogenation through Deoxygenation of Alcohols and Aldehydes

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Discovery and Optimization of Chromeno[2,3-c]pyrrol-9(2H)-ones as Novel Selective and Orally Bioavailable Phosphodiesterase 5 Inhibitors for the Treatment of Pulmonary Arterial Hypertension

Phosphodiesterase 5 (PDE5) inhibitors have been used as clinical agents to treat erectile dysfunction and pulmonary arterial hypertension (PAH). Herein, we detail the discovery of a novel series of chromeno[2,3-c]pyrrol-9(2H)-one derivatives as selective and orally bioavailable inhibitors against phosphodiesterase 5. Medicinal chemistry optimization resulted in 2, which exhibits a desirable inhibitory potency of 5.6 nM with remarkable selectivity as well as excellent pharmacokinetic properties and an oral bioavailability of 63.4%. In addition, oral administration of 2 at a dose of 5.0 mg/kg caused better pharmacodynamics effects on both mPAP (mean pulmonary artery pressure) and RVHI (index of right ventricle hypertrophy) than sildenafil citrate at a dose of 10.0 mg/kg. These activities along with its reasonable druglike properties, such as human liver microsomal stability, cytochrome inhibition, hERG inhibition, and pharmacological safety, indicate that 2 is a potential candidate for the treatment of PAH.