402-49-3

Usage

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

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

Downstream Products

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 30932-37-7 phenyl(4-(trifluoromethyl)benzyl)sulfane 
• 2338-75-2 4-(Trifluoromethyl)phenylacetonitrile 
• 98300-07-3 3-Cyano-1-(4-trifluoromethyl-benzyl)-pyridinium; bromide 
• 87861-96-9 3-Cyano-1-(4-trifluoromethyl-benzyl)-quinolinium; bromide 
• 87861-99-2 5-(4-Trifluoromethyl-benzyl)-phenanthridinium; bromide 
• 117775-93-6 4-(Trifluoromethyl)benzyl 4-nitrophenyl sulfide 
• 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 
• 1027068-58-1 4-[4-(4-Trifluoromethyl-benzyl)-benzoyl]-benzoic acid methyl ester 
• 61692-88-4 1-(3-phenylprop-2-yn-1-yl)-4-(trifluoromethyl)benzene 
• 61692-93-1 1-p-Trifluormethylphenyl-3-p-tolylpropin-3 
• 41499-20-1 p-Trifluormethylbenzylthiocyanat 
• 150109-61-8 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-trifluoromethyl-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

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.

Aryl Sulfonium Salts for Site-Selective Late-Stage Trifluoromethylation

Incorporation of the CF3 group into arenes has found increasing importance in drug discovery. Herein, we report the first photoredox-catalyzed cross-coupling of aryl thianthrenium salts with a copper-based trifluoromethyl reagent, which enables a site-selective late-stage trifluoromethylation of arenes. The reaction proceeds with broad functional group tolerance, even for complex small molecules on gram scale. The method was further extended to produce pentafluoroethylated derivatives.

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.

Synthesis and biological evaluation of curcumin inspired indole analogues as tubulin polymerization inhibitors

In our endeavour towards the development of potent cytotoxic agents, a series of some new curcumin inspired indole analogues, in which indole and phenyl moieties are linked on either sides of 1,5-diaryl-1,4-pentadien-3-one system have been synthesized and characterized by spectral data. All the newly synthesized analogues were tested for their cytotoxic potential against a panel of eight cancer cell lines namely, lung (A549), breast (MDA-MB-231, BT549 and 4T1), prostate (PC-3, DU145), gastric (HGC-27) and cervical (HeLa). Notably, among all the compounds tested, compounds 11c, 11d and 11f showed potent growth inhibition on PC-3 and BT549 with IC50values in the range of 3.12–6.34?μM and 4.69–8.72?μM respectively. The most active compound (11c) was also tested on RWPE-1 (normal prostate) cells and was found to be safe compared to the PC-3?cells. In tubulin polymerization assay, compounds 11c and 11f effectively inhibited microtubule assembly with IC50values of 10.21?±?0.10 and 8.83?±?0.06?μM respectively. The results from molecular modelling studies revealed that these compounds bind at the colchicine binding site of the tubulin. Moreover, DAPI and acridine orange/ethidium bromide staining studies indicated that compounds 11c and 11f can induce apoptosis in PC-3?cells. Further flow-cytometry analysis revealed that compound 11c arrests PC-3?cells in G2/M phase of the cell cycle while compound 11f treatment resulted in moderate increase in the G2/M population. Additionally, the treatment by these compounds led to the impairment of mitochondrial membrane potential (DΨm) in PC-3?cells.

Synthesis and Biological Evaluation of 1,2,3-triazole tethered Pyrazoline and Chalcone Derivatives

A series of pyrazoline derivatives and corresponding chalcone intermediates with substituents same as combretastatin-A4(CA-4) conjugated with triazole nucleus has been synthesized and evaluated for their anticancer potential. Sulphorhodamine B(SRB) assay indicated compound 12c to be the most active compound from the series with GI50 value of 6.7 μm against the human liver carcinoma cell line HepG2. Interestingly, the intermediate 11c exhibited more promising cytotoxicity demonstrating GI50 value of 1.3 μm against the prostate cancer cell line DU145. Compounds 11c and 12c caused accumulation of cells in G2/M phase and inhibited tubulin polymerization. Furthermore, these compounds reduce the mitochondrial membrane potential and activate caspases 3 and 9, thereby indicating their ability to trigger apoptosis.

Synthesis and biological evaluation of pyrazolo-triazole hybrids as cytotoxic and apoptosis inducing agents

A series of pyrazolo-triazole hybrids were designed and synthesized by combining the 1,3-diphenyl pyrazole and triazole scaffolds to obtain (1-benzyl-1H-1,2,3-triazol-4-yl)(1,3-diphenyl-1H-pyrazol-4-yl)methanones. All the synthesized compounds were screened for their anticancer activity against four tumor cell lines, viz. HT-29 (colon), PC-3 (prostate), A549 (lung), and U87MG (glioblastoma) cells. Most of the tested compounds showed moderate to potent cell growth inhibition on different cancer cells, in particular, the compounds 17, 23, and 29 exhibited promising cytotoxicity against these cell lines with the IC50 values in the range of 0.86-3.72 μM. In addition, the potential mechanism of cell growth inhibition and apoptotic induction by these compounds was investigated in U87MG cancer cells using cell-based assays, including wound healing assay, flow cytometry, Hoechst staining, acridine orange/ethidium bromide staining, Annexin V-FITC/propidium Iodide dual staining, Rhodamine 123 staining, and carboxy-DCFDA staining. The results indicate that the compounds induce apoptosis in U87MG cells via mitochondrial pathway through up-regulation of pro-apoptotic (Bax) and down-regulation of anti-apoptotic (Bcl-2) genes. Based on these studies, three compounds 17, 23 and 29 have been identified as promising new molecules that have the potential to be developed as leads.

Bulk photovoltaic effect in an organic polar crystal

Organic polar crystals from the donor-acceptor substituted 1,4-diphenybutadiene 1 can generate a short-circuit photocurrent and a photovoltage upon illumination with near UV light. The photocurrent and photovoltage are attributed to a bulk photovoltaic effect. The bulk photovoltaic effect has been known for inorganic polar crystals for decades and can now also be demonstrated for organic polar crystals. This journal is the Partner Organisations 2014.

Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles

A series of 5-nitrofuran-triazole conjugates were synthesized and evaluated for their antimicrobial activity against both Gram-positive and Gram-negative bacterial strains. All the compounds exhibited promising inhibition towards Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 8a, 8b, 8e, 8f, 8h are most active among the series exhibiting MIC value of 1.17 μg/ml against different bacterial strains. The bactericidal activity is found to be in accordance with the bacterial growth inhibition data. Compound 8e was found to be equipotent to the standard drug Ciprofloxacin displaying MBC value of 1.17 μg/ml against the bacterial strain Bacillus subtilis. The compounds have also demonstrated promising antibacterial activity against the resistant strain MRSA and were found to be effective inhibitors of biofilm formation. The compound 8b exhibited excellent anti-biofilm activity with IC50 value as low as 0.8 μg/ml. These conjugates were also screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. Compound 8e showed promising antitubercular activity with MIC value of 0.25 μg/ml. Most of these compounds are less toxic to normal mammalian cells than the widely used antibacterial drug Ciprofloxacin.

Indium(III)-catalyzed one-pot synthesis of alkyl cyanides from carboxylic Acids

The one-pot preparation of alkyl cyanides from carboxylic acids via alkyl iodides or alkyl bromides, which were in situ generated either by indium(III)-catalyzed reductive iodination or bromination of carboxylic acids, is described. Georg Thieme Verlag Stuttgart New York.