94569-84-3

Usage

Uses

Used in Material Science:
2-Bromo-5-fluorobenzaldehyde is used as a precursor for the synthesis of 5-fluoro-3-substituted benzoxaboroles, which serve as molecular receptors, building blocks in crystal engineering, and steroid conjugates for molecular imprinting. These benzoxaboroles are also utilized in the development of dyes and biosensors for alpha-hydroxyl carboxylic acids.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromo-5-fluorobenzaldehyde is used in the synthesis of 5-arylindazolo[3,2-b]quinazolin-7(5H)-one by reacting with 2-amino-N'-arylbenzohydrazide in the presence of Copper(I) bromide through a Ullmann-type reaction. This synthesized compound may have potential applications in drug discovery and development.
Used in Organic Synthesis:
2-Bromo-5-fluorobenzaldehyde may also be used in the synthesis of dihydrobenzoxaboroles bearing aryl, heteroaryl, or vinyl substituents at the 1-position and 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole. These compounds can be employed as intermediates in the development of various organic compounds and materials.

InChI:InChI=1/C7H4BrFO/c8-7-2-1-6(9)3-5(7)4-10/h1-4H

Upstream product

• 112399-50-5 2-bromo-5-fluorobenzyl bromide 
• 866029-28-9 2-(2-bromo-5-fluorophenyl)ethan-1-ol 
• 1069115-12-3 methyl 2-(2-bromo-5-fluorophenyl)acetate 
• 739336-26-6 2-(2-bromo-5-fluorophenyl) acetic acid 
• 202865-66-5 2-bromo-5-fluorobenzyl alcohol 
• 456-48-4 3-Fluorobenzaldehyde 
• 543730-68-3 3-fluorobenzaldehyde O-methyloxime 
• 452-63-1 2-Bromo-5-fluorotoluene 
• 68-12-2 N,N-dimethyl-formamide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 6942-39-8 methyl 2-bromo-5-fluorobenzoate 

Downstream Products

• 943835-77-6 5-fluoro-2-(2-phenylethynyl)benzaldehyde 
• 174671-46-6 tavaborole 
• 933585-18-3 1-bromo-2-(dimethoxymethyl)-4-fluorobenzene 
• 1154595-29-5 6-((4-fluoro-2-formylphenyl)ethynyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 1184663-67-9 C₂₆H₂₇FNO₄P 
• 1258856-98-2 C₁₆H₁₂FN 
• 1256164-73-4 1-(2-bromo-5-fluorophenyl)-1-hydroxy-4-phenylbutan-2-one 
• 1282499-17-5 C₁₄H₁₂BrFO 
• 1283494-80-3 C₁₄H₁₂BrFO₂ 
• 343-01-1 2-fluoro-9H-fluoren-9-one 
• 1383456-26-5 (R)-7-fluoro-1-(1H-indol-3-yl)-3-phenyl-2-tosyl-1,2-dihydroisoquinoline 
• 1383456-19-6 N-(5-fluoro-2-(phenylethynyl)benzylidene)-4-methylbenzenesulfonamide 
• 1006-33-3 1-(2′-bromo-5′-fluorophenyl)ethan-1-one 
• 1350844-26-6 1-(5-fluoro-2-(pent-1-ynyl)phenyl)ethanone 

Relevant academic research and scientific papers

Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light

Synthesis of new Schiff's base Zn-complexes for photo-oxidation of methyl arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of methyl arenes which are converted into its respective aldehydes with moderate yields under visible light irradiation. The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the methyl groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of methyl arenes is reported under visible-light-driven conditions.

Synthesis and inhibitory studies of phosphonic acid analogues of homophenylalanine and phenylalanine towards alanyl aminopeptidases

A library of novel phosphonic acid analogues of homophenylalanine and phenylalanine, containing fluorine and bromine atoms in the phenyl ring, have been synthesized. Their inhibitory properties against two important alanine aminopeptidases, of human (hAPN, CD13) and porcine (pAPN) origin, were evaluated. Enzymatic studies and comparison with literature data indicated the higher inhibitory potential of the homophenylalanine over phenylalanine derivatives towards both enzymes. Their inhibition constants were in the submicromolar range for hAPN and the micromolar range for pAPN, with 1-amino-3-(3-fluorophenyl) propylphosphonic acid (compound 15c) being one of the best low-molecular inhibitors of both enzymes. To the best of our knowledge, P1 homophenylalanine analogues are the most active inhibitors of the APN among phosphonic and phosphinic derivatives described in the literature. Therefore, they constitute interesting building blocks for the further design of chemically more complex inhibitors. Based on molecular modeling simulations and SAR (structure-activity relationship) analysis, the optimal architecture of enzyme-inhibitor complexes for hAPN and pAPN were determined.

Based on 4 - phenyl -6 - (2, 2, 2 - trifluoro -1 - phenyl ethoxy) pyrimidine compound and its application method

The present invention relates to compounds based on 4-phenyl-6-(2,2,2-trifluoro-1-phenyl ethoxy) pyrimidine and an application method thereof, particularly discloses compounds of formula I and compositions comprising the compounds, and the application method thereof in treatment, prevention and / or management of diseases or disorders.

Synthesis of smart bimetallic nano-Cu/Ag@SiO2 for clean oxidation of alcohols

Here, we have demonstrated the synthesis and characterization of silica supported bimetallic copper/silver nanoparticles (Cu/Ag@SiO2 NPs) and their application in the clean oxidation of benzoins/benzyl alcohols in the presence of tert-butyl hydroperoxide as a mild oxidant. All the reactions were very fast (4 h) and high yielding (95-99%), and the Cu/Ag@SiO2 NPs were very stable under the reaction conditions. The catalyst was recovered simply by filtration and reused eight times without loss of its catalytic performance.

A gold catalytic oxidation of benzyl alcohol synthesis method (by machine translation)

The present invention provides a kind of organic synthesis in the oxidation of benzyl alcohol synthesis method, the reaction formula is as follows, in the formula 1 containing different substituents is benzyl alcohol, in the formula 2 is triphenylcarbinol compound. The required reaction of gold catalyst is Ph3 PAuCl, Ph3 PAuNTf2 , HAuCl4 , NaAuCl4 , Ph3 PAuOTf, Ph3 PAuSbF6 , IPrAuCl, gold. The required reaction medium is: solvent-free, toluene, are three-toluene, 1, 2 - dichloroethane, tetrahydrofuran, acetonitrile, acetone. The reaction implementing microwave heating of reactor, the method of the invention the oxidizing agent triphenylcarbinol for commercial products, cheap, and simple experimental operation, substrate and wide range of application. (by machine translation)

Fe(III)-catalyzed trityl benzyl ether formation and disproportionation cascade reactions to yield benzaldehydes

During investigating water-compatible Lewis acids catalyzed etherifications using alcohols as alkylating reagents directly, we developed Fe(III)-catalyzed trityl benzyl ether formations irradiated by microwave. Then an in situ trityl benzyl ether formation and disproportionation cascade reaction was achieved to yield the benzaldehyde products with good functional group tolerances under neat conditions at relative higher temperatures. The substituent effects of the substrates on the etherification and disproportionation were explored by changing the substitutions on benzyl alcohols and triarylmethanols using chemical kinetic plots methods and the mechanism of the transformation was studied by crossover experiments. The etherification and disproportionation cascade process could be conveniently scaled up in laboratory without losing much efficiency.

TEMPO-mediated oxidation of primary alcohols to aldehydes under visible light and air

A homogeneous visible light photoredox TEMPO-mediated selective oxidation of primary alcohols to the corresponding carbonyl compounds was developed using molecular oxygen from air as the terminal oxidant. Ru(bpy)3(PF 6)2 (bpy: bipyridyl) and Ir(dtb-bpy)(ppy) 2(PF6) (dtb-bpy: 4,4′-di-tert-butyl-2,2′- bipyridyl; ppy: 2-phenylpyridine) were used as the sensitizers. A homogeneous visible light photoredox TEMPO-mediated selective oxidation of primary alcohols to the corresponding carbonyl compounds was developed. Molecular oxygen from air was the terminal oxidant. Copyright

IBX works efficiently under solvent free conditions in ball milling

IBX (2-iodoxybenzoic acid), discovered in 1893, is an oxidant in synthetic chemistry whose extensive use is impeded by its explosiveness at high temperature and poor solubility in common organic solvents except DMSO. Since the discovery of Dess-Martin Periodinane in 1983, several modified IBX systems have been reported. However, under ball milling conditions, IBX works efficiently with various organic functionalities at ambient temperature under solvent free conditions. Also, the waste IBA (2-iodosobenzoic acid) produced from the reactions was in situ oxidized to IBX in the following step using oxone and thus reused for multiple cycles by conserving its efficiency (only ～6% loss after 15 cycles). This work describes an overview of a highly economical synthetic methodology which overcomes the problems of using IBX, efficiently in gram scale and in a non-explosive way. This journal is the Partner Organisations 2014.

Silver-catalyzed stereoselective [3+2] cycloadditions of cyclopropyl-indanimines with carbonyl compounds

Silver-catalyzed stereoselective [3+2] cycloadditions between mono-substituted cyclopropyl-indanimines and aldehydes are reported. The stereochemical course of the reaction is rationalized with a cyclic transition state. The resulting indanimine cycloadducts are not readily hydrolyzed unless external aldehydes are present with the silver catalyst. Notably, this hydrolysis process leads to a change of stereochemistry for the resulting indanone products. Copyright

Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration

A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.