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

Uses

Different sources of media describe the Uses of 402-49-3 differently. You can refer to the following data:
1. 4-(Trifluoromethyl)benzyl Bromide is a useful building block. It is used in the synthesis of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles with antiviral activities.It is also used to prepare 2-[(4-diarylmethoxy)phenyl]benzimidazoles as potent inhibitors of hepatitis C virus NS5B polymerase.
2. 4-(Trifluoromethyl)benzyl bromide can be used to produce p-trifluoromethylbenzyl phenyl sulfide. It is used in medicine.

General Description

Vibrational characteristics of 4-(trifluoromethyl)benzylbromide have been investigated.

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

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 2338-75-2 4-(Trifluoromethyl)phenylacetonitrile 
• 38733-98-1 4-(trifluoromethyl)benzyltriphenylphosphonium bromide 
• 132549-56-5 <(3-(p-Trifluoromethyl)-benzylcamphoryl)>imine 
• 1026577-21-8 [3-Benzyloxycarbonylamino-2-oxo-5-(4-trifluoromethyl-benzyl)-2H-pyridin-1-yl]-acetic acid ethyl ester 
• 41499-20-1 p-Trifluormethylbenzylthiocyanat 
• 108868-46-8 1,3-Bis<4-(trifluoromethyl)phenyl>acetone 

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.