7745-93-9

Usage

InChI:InChI=1/C7H6BrNO2/c1-5-2-3-6(9(10)11)4-7(5)8/h2-4H,1H3

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 10035-10-6 hydrogen bromide 
• 95-46-5 2-methylphenyl bromide 
• 534-52-1 6-methyl-2,4-dinitrophenol 
• 7697-37-2 nitric acid 
• 95-48-7 ortho-cresol 
• 108-95-2 phenol 
• 121-14-2 2,4-dinitrotoluene 
• 67614-05-5 4-methylaniline hydrobromide 
• 7726-95-6 bromine 
• 121-03-9 4-nitrotoluene-2-sulfonic acid 
• 7705-08-0 iron(III) chloride 
• 99-55-8 2-methyl-5-nitroaniline 
• 827-32-7 4-bromo-5-methyl-2-nitrophenylamine 

Downstream Products

• 13480-38-1 4-Nitro-2-phenyltoluene 
• 248602-16-6 6-bromo-5-methyl-1H-indole 
• 7745-91-7 3-bromo-4-methylaniline 
• 655248-57-0 4-amino-2-bromo-benzaldehyde 
• 470715-98-1 acetic acid acetoxy-(2-bromo-4-nitro-phenyl)-methyl ester 
• 92-52-4 biphenyl 
• 40371-61-7 N-(3-bromo-4-methyl-phenyl)acetamide 
• 785775-72-6 4-[(5-amino-3'-methoxy-biphenyl-2-ylmethoxy)-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile 
• 773848-01-4 4-[(3'-methoxy-5-nitro-biphenyl-2-ylmethoxy)-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile 
• 858681-96-6 tert-butyl 4-(5-nitro-2-methylphenyl)-3,6-dihydro-1(2H)-pyridine carboxylate 
• 267648-14-6 3-bromo-4-(oxazol-5-yl)aniline 
• 939-83-3 2-cyano-4-nitrotoluene 
• 1427-07-2 2-fluoro-4-nitrotoluene 
• 1344109-43-8 2-bromo-4-(pyrrol-1-yl)benzoic acid methyl ester 

Relevant academic research and scientific papers

Nitration of deactivated aromatic compounds via mechanochemical reaction

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

Preparation method of 2 -bromo -4-chlorobenzaldehyde

The invention relates to a preparation method of 2 -bromo -4-chlorobenzaldehyde and belongs to the field of medicinal chemistry. The preparation method can obtain 2 -bromo -4-chlorobenzaldehyde by taking nitrotoluene as a starting material through substitution, reduction, substitution, substitution, substitution, hydrolysis and elimination reaction. Compared with the prior art, the method shortens the reaction time, the reaction temperature is higher 120 °C or higher, the reaction conditions are mild, the yield of the obtained product is about 70% and more than 90%. The reaction temperature is reduced, high-boiling-point solvent is not needed to participate in the reaction, the post-treatment is simple, and the method is more suitable for industrial production with strict safety and environmental protection.

Design, synthesis and anti-inflammatory activity of pyrimidine scaffold benzamide derivatives as epidermal growth factor receptor tyrosine kinase inhibitors

Novel serious of pyrimidine scaffold benzamide derivatives (9 a-k) were synthesized and characterized by IR, HRMS, and NMR. Docking study of compounds 9 g, 9 h exhibited H-bonding interacts with Met769 into ATP binding site of EGFR-TK which showed similar binding mode to Lapitinib (PDB code: 1M17). Results indicated the ability to potent and selective inhibitors of the Epidermal Growth Factor Receptor tyrosine kinase (EGFR-TK). The molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs) and HOMO-LUMO energy gap of the title compounds were investigated by using the B3LYP/6-31G method. The synthesized compounds were screened for in vitro anti-inflammatory activity.

Design, Synthesis, and Evaluation of the Kinase Inhibition Potential of Pyridylpyrimidinylaminophenyl Derivatives

In view of potent kinase inhibitors for the treatment of myriad human disorders, we synthesized some structurally variant amide/cyclic amide derivatives based on pyridylpyrimidinylaminophenyl amine, the key pharmacophore of the kinase inhibitor drug molecule, imatinib, and evaluated their kinase inhibition potency. Among the various synthesized amides, compound 20, a cyclic amide/pyridin-2(1H)-one derivative, exhibited an IC50 value comparable to that of the drug imatinib against c-Src kinase, and another compound (14) containing a 2-((4-methyl-2-oxo-2H-chromen-6-yl)oxy)acetamide demonstrated an IC50 value of 8.39 μM. Furthermore, the constitution of the cyclic amide derivative was confirmed by the single-crystal X-ray diffraction technique. These results may serve as a gateway for developing novel next-generation kinase inhibitors.

Reactivity of alkali and alkaline earth metal tetrafluorobromates towards aromatic compounds and pyridine

The bromination activity of tetrafluorobromates of alkali and alkali-earth metals increases in the order KBrF4, CsBrF4, RbBrF4and Ba(BrF4)2. The most active tetrafluorobromate—Ba(BrF4)2is able to selectively brominate the deactivated aromatic compounds nitrobenzene and 4-nitrotoluene, but not the activated compounds benzene and toluene. In all cases bromination of methyl groups of methylbenzenes does not occur. Ba(BrF4)2forms the known complex C6H5N·BrF3when reacted with pyridine. Due to dilution by inert BaF2, this pyridine-based complex is air stable and can be considered as safer and more convenient reagent in comparison with the original fluorobromates; it can selectively brominate benzene and toluene in contrast with tetrafluorobromates.

Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes

Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H 2SO4. Georg Thieme Verlag Stuttgart · New York.

Thallium(III) oxide as an oxidative reagent in organic chemistry

Oxidative properties of thallium(III) oxide in various organic reactions were studied. Oxidative bromination of organic compounds in Tl2O 3-KBr-trifluoroacetic acid system was carried out. New synthetic method for preparation of diphenylthallium salts from phenylhydrazine and thallium(III) oxide was developed.

A facile total synthesis of imatinib base and its analogues

Imatinib and its analogues were successfully synthesized by an improved method in 19.5-46.2% total yield of six main steps. Pyrimidinyl amine was prepared by the reaction of enaminone and guanidine nitrate without the use of a toxic cyanamide. N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl) pyrimidin-2-amine as a key intermediate for the synthesis of imatinib was prepared by coppercatalyzed iV-arylation of heteroarylamme in 82% yield. The copper salts were used instead of the expensive palladium compounds in this C-N bond-forming reaction. The intermediate nitro compound was reduced by a N2H 4.H2O/FeCl3/C system using water as a solvent in good yield.

Electronic effects of ring substituents on triplet benzylic biradicals

UV irradiation of α-(o-alkylphenyl)acetophenones with a methoxy or cyano substituent para to the o-alkyl group of the α-aryl ring has revealed that a methoxy group slightly increases the stereoselectivity but not the quantum yield of indanol formation, whereas a cyano group greatly lowers both diastereoselectivity and quantum efficiency, confirming the likelihood that hydrogen-bonding of the hydroxy group to the α-phenyl ring plays an important role in the cyclization of the photogenerated triplet 1,5-biradical intermediates.

Reaction of dimethyldioxirane with aniline hydrohalides

Oxidation of aromatic amine hydrohalides (aniline hydrochloride, hydrobromide, and hydrofluoride; 4-methylaniline hydrochloride and hydrobromide; 3-methylaniline and N,N-diethylaniline hydrochlorides) with dimethyldioxirane was studied. The product composition was analyzed in relation to the reactant ratio.