7154-66-7

Usage

Chemical Properties

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

InChI:InChI=1/C7H4BrClO/c8-6-4-2-1-3-5(6)7(9)10/h1-4H

Upstream product

• 79-37-8 oxalyl dichloride 
• 88-65-3 2-bromobenzoic-acid 
• 108-86-1 bromobenzene 
• 586-76-5 4-Bromobenzoic acid 
• 7719-12-2 phosphorus trichloride 
• 118-92-3 anthranilic acid 
• 55666-42-7 tert-butyl 2-bromobenzoate 

Downstream Products

• 2142-69-0 2-bromophenyl methyl ketone 
• 2178-24-7 ethyl 2-(2-bromophenyl)ethanoate 
• 46004-44-8 2-bromo-ω-diazoacetophenone 
• 61153-35-3 (2-bromophenyl)(piperidin-1-yl)methanone 
• 136926-09-5 2-bromo-N-(4-methylphenyl)benzamide 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 55270-73-0 (2-bromophenyl)(2-hydroxy-5-methylphenyl)methanone 
• 23346-79-4 (2-bromophenyl)-(3,4-dimethoxyphenyl)methanone 
• 80874-61-9 [1,1'-biphenyl]-4-yl(2-bromophenyl)methanone 
• 855260-59-2 4,4'-bis-(2-bromo-benzoyl)-biphenyl 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 79713-34-1 1-(2-bromo-phenyl)-3t-chloro-propenone 
• 951891-12-6 2-bromo-4'-chloro-3'-methyl-benzophenone 

Relevant academic research and scientific papers

Cavity-extended inherently chiral resorcin[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers

Inherently chiral resorcin[4]arenes 2 and 3 were prepared from enantiomerically pure C4-symmetric rccc-2,8,14,20-tetraisobutyl-4,10, 16,22-tetra-O-methylresorcin[4]arene (1). The four 2-bromobenzyl ether residues in precursor 2 were introduced

Stereoinvertive C–C Bond Formation at the Boron-Bound Stereogenic Centers through Copper-Bipyridine-Catalyzed Intramolecular Coupling of α-Aminobenzylboronic Esters

Enantiospecific intramolecular Suzuki–Miyaura-type coupling with α-(2-halobenzoylamino)benzylboronic esters to give 3-substituted isoindolinones is achieved by using copper catalysts with 2,2′-bipyridine-based achiral ligands. Enantioenriched α-aminobenzylboron reactants bearing a hydrogen atom at the boron-bound stereogenic carbons undergo stereoinvertive coupling in the presence of a 6-phenyl-2,2′-bipyridine ligand with high enantiospecificity. α-Aminobenzylboronates bearing fully substituted boron-bound stereogenic centers also gave the 3,3-disubstituted isoindolinones with stereospecific stereochemical inversion in the presence of simple 2,2′-bipyridine as a ligand.

6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine

Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

Method for synthesizing chlorantraniliprole derivative intermediate

The invention provides a method for synthesizing a chlorantraniliprole derivative intermediate, belonging to the field of agricultural pesticides. The method comprises the following steps: subjectingthe intermediate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid to chlorination so as to prepare 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-formyl chloride; subjecting the raw material 2-bromobenzoic acid to acylating chlorination and ammoniation so as to prepare substituted 2-bromo-benzamide; and subjecting 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-formyl chloride and substituted 2-bromo-benzamide to cyclization so as to obtain the chlorantraniliprole derivative intermediate. The method of the invention is simple and common; reagents used in the process of synthesis are low in toxicity, used solvents are recyclable, and few by-products are produced, so the method has little corrosion to equipment and low pollution to environment; since raw materials are cheap, production cost is reduced and good economical efficiency is obtained; therefore, the method has good application prospects.

The Conversion of tert-Butyl Esters to Acid Chlorides Using Thionyl Chloride

The reaction of tert-butyl esters with SOCl2 at room temperature provides acid chlorides in unpurified yields of 89% or greater. Benzyl, methyl, ethyl, and isopropyl esters are essentially unreactive under these conditions, allowing for the selective conversion of tert-butyl esters to acid chlorides in the presence of other esters.

Design, synthesis and antibacterial activity of isatin derivatives as FtsZ inhibitors

Seven isatin derivatives have been designed, and their chemical structures were characterized by single crystal X-ray diffraction studies, 1H NMR, MS, and elemental analysis. Structural stabilization followed by intramolecular as well as intermolecular H-bonds makes these molecules as perfect examples in molecular recognition with self-complementary donor and acceptor units within a single molecule. These compounds were evaluated for antimicrobial activities. Docking simulations have been performed to position compounds into the FtsZ active site to determine their probable binding models. All of the compounds exhibited better antibacterial activities. Interestingly, compound 5c and 5d exhibited better antibacterial activities with IC50 values of 0.03 and 0.05 μmol/mL against Staphylococcus aureus, respectively. Compound 5g displays antibacterial activity with IC50 values of 0.672 and 0.830 μmol/mL against Escherichia coli and Pseudomonas aeruginosa, respectively.

Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones

Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.

Unprecedented Formation of π-Copper Complexes during Sonogashira Coupling: Synthesis of a Unique, Recyclable, Ethynyl Ferrocene Derived Cu(I) Specific Ligand

During the synthesis of a chiral oxazolinyl-derived ethynyl ferrocene {Fc-C≡C-C6H4-o-(4-iPr-2-Ox)} (Fc = ferrocenyl; Ox = oxazolinyl), we observed an unprecedented formation of highly air stable and monomeric π-copper(I) complexes 4a and 4b, which were structurally characterized. CuI was used as a cocatalyst in this Sonogashira coupling. By the reaction of 4a with aqueous NH3/DMF, the CuI was removed from the complex and the metal-free compound 5a was obtained. This was found to be an excellent ligand for selectively binding Cu(I) halides. Analogous 4-Ph-substituted oxazoline-based ligand 5b and its Cu-I complex 4c were also isolated and characterized. The possible role of these complexes in explaining the copper cycle proposed for Sonogashira coupling has also been discussed.

Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis of quinazolinones

A series of bioactive quinazolinones were effectively synthesized by the condensation of halide benzamide with amino acid using magnetically recyclable GO/Fe3O4-CuI as catalyst. Magnetic GO/Fe3O4-CuI was prepared via a simple chemical method and characterized by FTIR, powder XRD, and SEM. This heterogeneous copper catalyst can be easily separated from reaction mixtures by an external permanent magnet and reused without any obvious loss in activity which shows its applicability as a reusable and promising catalyst for quinazolinones synthesis.