50824-05-0

Basic information

• Product Name: 4-(Trifluoromethoxy)benzyl bromide
• Synonyms: 4-(TRIFLUOROMETHOXY)BENZYL BROMIDE;ALPHA-BROMO-4-(TRIFLUOROMETHOXY)TOLUENE;1-(BROMOMETHYL)-4-(TRIFLUOROMETHOXY)BENZENE;TIMTEC-BB SBB006578;P-TritluromethoxybenzylBromide;4-(Trifluoromethoxy)benzyl;4-(Trifluoromethoxy)benzyl bromide 97%;4-(Trifluoromethoxy)benzylbromide97%
• CAS NO: 50824-05-0
• Molecular Formula: C₈H₆BrF₃O
• Molecular Weight: 255.03
• Product Categories: Aromatic Halides (substituted);Miscellaneous;Ethers;Organic Building Blocks;Oxygen Compounds;Trifluoro-methoxy-benzene series
• Mol File: 50824-05-0.mol

Chemical Properties

• Melting Point: 22-24°C
• Boiling Point: 82-84 °C10 mm Hg(lit.)
• Flash Point: 202 °F
• Appearance: Clear faintly yellow/Liquid or Low Melting Solid
• Density: 1.594 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.44mmHg at 25°C
• Refractive Index: n20/D 1.48(lit.)
• Storage Temp.: Refrigerated.
• Sensitive: Lachrymatory
• BRN: 2521451
• CAS DataBase Reference: 4-(Trifluoromethoxy)benzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethoxy)benzyl bromide(50824-05-0)
• EPA Substance Registry System: 4-(Trifluoromethoxy)benzyl bromide(50824-05-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 50824-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(Trifluoromethoxy)benzyl bromide is used as a synthetic intermediate for the preparation of various pharmaceutical compounds with therapeutic applications. It is particularly utilized in the synthesis of (nitro)[(trifluoromethoxy)benzyloxy]dihydroimidazo[2,1-b][1,3]oxazines, which exhibit antitubercular activities, and tetrahydronaphthalenols, which possess anti-allergic properties.
Used in Synthesis of Bioreductive Drug:
In the pharmaceutical industry, 4-(Trifluoromethoxy)benzyl bromide is also employed in the synthesis of the bioreductive drug, (6S)-2-nitro-6-[4-(trifluoromethoxy)benzyl]oxy-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824), which has potential applications in cancer treatment.
Used in Chemical Synthesis:
4-(Trifluoromethoxy)benzyl bromide is used as a monomer in the chemical industry, where it undergoes polymerizations via Friedel-Crafts polymerization using aluminum chloride as a catalyst. This process allows for the creation of polymers with specific properties and applications in various fields.

InChI:InChI=1/C9H7F9O2/c1-2-5(19)20-4-3-6(10,11)7(12,8(13,14)15)9(16,17)18/h2H,1,3-4H2

Upstream product

• 1736-74-9 4-trifluoromethoxybenzyl alcohol 
• 587-18-8 4-trifluoromethoxy-benzoic acid ethyl ester 
• 456-55-3 1-trifluoromethoxybenzene 
• 659-28-9 p-trifluoromethoxybenzaldehyde 

Downstream Products

• 49561-96-8 (4-trifluoromethoxy-phenyl)-acetonitrile 
• 340759-27-5 1-(4-(trifluoromethoxy)benzyl)piperazine 
• 280135-08-2 5-(4-trifluoromethoxybenzyloxy)methyl-1-naphthaldehyde 
• 616882-14-5 N-tert-butoxycarbonylamino-O-(4-trifluoromethoxybenzyl)-D-serine 
• 632626-49-4 3-{2-[5-bromo-2-(4-trifluoromethoxybenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-benzoic acid ethyl ester 
• 916044-94-5 5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(4-trifluoromethoxy-benzyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole 
• 950201-44-2 C₁₅H₁₁F₃N₂O₃ 
• 954386-76-6 5-Nitro-1-(4-(trifluoromethoxy)benzyl)-1H-indole 
• 1000773-52-3 2-[(1-(4-trifluoromethoxy-benzyloxy)-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester 
• 921623-40-7 tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate 

Relevant articles and documents

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.

Iron-catalyzed borylation of alkyl, allyl, and aryl halides: Isolation of an iron(I) boryl complex

Activation of B2pin2 with tBuLi facilitates the Fe-catalyzed borylation of alkyl, allyl, benzyl, and aryl halides via the formation of Li[B2pin2(tBu)] (1). The reaction of 1 with a representative iron phosphine precatalyst generates the unique iron(I) boryl complex [Fe(Bpin)(dpbz)2] (2).

SULFONYL-SUBSTITUTED BICYCLIC COMPOUNDS AS MODULATORS OF PPAR

The present invention relates to compounds and methods useful as inhibitors of PPAR, particularly PPARδ, and for the treatment or prevention of PPAR-mediated diseases, including metabolic diseases.

Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety

By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4-methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G2/M arrest of the cell cycle in human cancer cells.

PROCESS FOR PREPARING 2-(4-TRIFLUOROMETHOXYPHENYL)ETHYLAMINE AND 4-BROMOMETHYL-AND 4-CHLOROMETHYL-1-TRIFLUOROMETHOXYBENZENE

The invention relates to a process for preparing 2-(4-trifluoromethoxyphenyl)ethylamine in an advantageous manner by (a) converting trifluoromethoxybenzene by halomethylation into halogenomethyl-1-trifluoromethoxybenzene, (b) converting the halogenomethyl

DIPHENYLETHANE DERIVATIVES

Diphenylethane derivatives of the formula are described; wherein R1 is a heterocyclyl radical selected from the group consisting of 1,2,4-triazolyl, optionally-substituted imidazolyl, pyridyl and pyrimidinyl radicals; R2 and R3, which may be the same or d