321-23-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoro-4-bromonitrobenzene is used as a building block for the synthesis of fused aromatic and heteroaromatic compounds, which are essential in the development of new drugs and pharmaceutical agents. Its unique structure allows for the creation of complex molecules with specific biological activities, making it a valuable component in medicinal chemistry.
Used in Chemical Industry:
In the chemical industry, 2-Fluoro-4-bromonitrobenzene can be utilized as an intermediate for the production of various specialty chemicals, dyes, and pigments. Its versatile structure enables it to be a key component in the synthesis of a wide range of compounds with different properties and applications.
Used in Research and Development:
2-Fluoro-4-bromonitrobenzene is also used as a research compound in academic and industrial laboratories. Its unique properties make it an interesting subject for studying various chemical reactions and exploring new synthetic pathways. This can lead to the discovery of novel compounds with potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C6H3BrFNO2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H

Upstream product

• 610-38-8 4-bromo-1,2-dinitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 1073-06-9 3-fluorobromobenzene 
• 348-54-9 2-Fluoroaniline 
• 367-24-8 4-bromo-2-fluoroaniline 

Downstream Products

• 189187-32-4 2-Fluoro-4-(diphenylmethyl)nitrobenzene 
• 883500-73-0 5-bromo-7-fluoro-1H-indole 
• 304875-15-8 5-(3-fluoro-4-nitrophenyl)spiro[cyclohexane-1,3-[3H]indole]-2(1H)-one 
• 305790-83-4 [(5-Bromo-2-nitro-phenyl)-isopropyl-amino]-acetic acid 
• 305790-76-5 N-(5-bromo-2-nitro-phenyl)-pyrrolidine-2-carboxylic acid 
• 305790-81-2 [(5-bromo-2-nitro-phenyl)-n-butyl-amino]acetic acid 
• 305790-78-7 [(5-bromo-2-nitro-phenyl)-methyl-amino]-acetic acid 
• 854044-45-4 1-(5-bromo-2-nitro-phenyl)-4-methyl-piperidine 
• 197777-90-5 3-fluoro-4-nitrostyrene 
• 103966-66-1 4-bromo-2-methoxy-1-nitro-benzene 
• 932700-66-8 N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine 
• 57279-70-6 4-bromo-2-ethoxy-1-nitro-benzene 
• 863605-02-1 5-bromo-N-isobutyl-2-nitroaniline 
• 1093763-54-2 C₁₅H₁₂BrNO₄ 

Relevant academic research and scientific papers

Synthesis and in Vitro Evaluation of 8-Pyridinyl-Substituted Benzo[e]imidazo[2,1-c][1,2,4]triazines as Phosphodiesterase 2A Inhibitors

Phosphodiesterase 2A (PDE2A) is highly expressed in distinct areas of the brain, which are known to be related to neuropsychiatric diseases. The development of suitable PDE2A tracers for Positron Emission Tomography (PET) would permit the in vivo imaging of the PDE2A and evaluation of disease-mediated alterations of its expression. A series of novel fluorinated PDE2A inhibitors on the basis of a Benzoimidazotriazine (BIT) scaffold was prepared leading to a prospective inhibitor for further development of a PDE2A PET imaging agent. BIT derivatives (BIT1–9) were obtained by a seven-step synthesis route, and their inhibitory potency towards PDE2A and selectivity over other PDEs were evaluated. BIT1 demonstrated much higher inhibition than other BIT derivatives (82.9% inhibition of PDE2A at 10 nM). BIT1 displayed an IC50 for PDE2A of 3.33 nM with 16-fold selectivity over PDE10A. This finding revealed that a derivative bearing both a 2-fluoro-pyridin-4-yl and 2-chloro-5-methoxy-phenyl unit at the 8- and 1-position, respectively, appeared to be the most potent inhibitor. In vitro studies of BIT1 using mouse liver microsomes (MLM) disclosed BIT1 as a suitable ligand for 18F-labeling. Nevertheless, future in vivo metabolism studies are required.

Sulfide Analogues of Flupirtine and Retigabine with Nanomolar KV7.2/KV7.3 Channel Opening Activity

The potassium channel openers flupirtine and retigabine have proven to be valuable analgesics or antiepileptics. Their recent withdrawal due to occasional hepatotoxicity and tissue discoloration, respectively, leaves a therapeutic niche unfilled. Metabolic oxidation of both drugs gives rise to the formation of electrophilic quinones. These elusive, highly reactive metabolites may induce liver injury in the case of flupirtine and blue tissue discoloration after prolonged intake of retigabine. We examined which structural features can be altered to avoid the detrimental oxidation of the aromatic ring and shift oxidation toward the formation of more benign metabolites. Structure–activity relationship studies were performed to evaluate the KV7.2/3 channel opening activity of 45 derivatives. Sulfide analogues were identified that are devoid of the risk of quinone formation, but possess potent KV7.2/3 opening activity. For example, flupirtine analogue 3-(3,5-difluorophenyl)-N-(6-(isobutylthio)-2-(pyrrolidin-1-yl)pyridin-3-yl)propanamide (48) has 100-fold enhanced activity (EC50=1.4 nm), a vastly improved toxicity/activity ratio, and the same efficacy as retigabine in vitro.

Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A

Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.

Oxidation of aromatic amines into nitroarenes with m-CPBA

A versatile and highly efficient approach for the synthesis of nitroarenes from aromatic amine using m-CPBA has been developed. This oxidation reaction was operationally straightforward and proceeded to afford products in good isolated yields.

HOMOGENEOUS TIME RESOLVED FLUORESCENCE BASED TEST SYSTEM

The present invention concerns a fluorescence resonance energy transfer based high throughput test system to measure the formation of the HIV gp41 six-helix bundle. In a first embodiment the current invention relates to a homogeneous time resolved fluorescence-based test system comprising a first helical polypeptide consisting essentially of the sequence of IQN36 (SEQ ID NO:1); a second helical polypeptide consisting essentially of the sequence of C34 (SEQ ID NO: 2) wherein said IQN36 is labeled with a light emitting fluorophore and said C34 is labeled with an ultra-violet excitable fluorophore.

BENZIMIDAZOLYL COMPOUNDS AS POTENTIATORS OF MGLUR2 SUBTYPE OF GLUTAMATE RECEPTOR

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

BENZIMIDAZOLYL COMPOUNDS

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of formula (I) or pharmaceutically acceptable salts thereof, wherein Y1, R17, R2, R4, R5, R6, R7, R8, X2 and n are as defined in the detailed description of the invention. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

Electrochemical fluorination of aromatic compounds in anhydrous HF

Electrochemical fluorination of anisole furnished 2- and 4-fluoroanisoles in a 3:1 ratio, guaiacol, and 4,4′-dimethoxydiphenyl ether. Phenylacetonitrile alongside the fluorination in the ring suffered the transformation of the cyano group into a trifluoromethyl. 4-Bromobenzamide was fluorinated to a high conversion mostly in the ring to afford predominantly 4-bromo-3,3,6,6-tetrafluoro-1,4-cyclohexadienecarboxamide. 4-Bromonitrobenzene in a low yield gave 4-bromofluoronitrobenzene and 3,4-dibromofluoronitrobenzene. 3-Bromo-nitrobenzene and 1,4-dichlorobenzene did not undergo fluorination. In the course of the electrolysis of the 4-bromobenzamide and 4-bromonitrobenzene in anhydrous HF apart the fluorination occurred also the bromination of the substrates. Pleiades Publishing, Inc. 2006.

In search of simplicity and flexibility: A rational access to twelve fluoroindolecarboxylic acids

All twelve indolecarboxylic acids 1-12 carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepared either directly from the corresponding fluoroindoles 13-16 or from the chlorinated derivatives 22, 23 and 25 by hydrogen/metal permutation ("metalation"), or from the bromo- or iodofluoroindoles 17-20 and 26, 27, 29 and 30 by halogen/metal permutation, the organometallic intermediate being each time trapped with carbon dioxide. In most, though not all cases, the nitrogen atom in the five-membered ring had to be protected by a trialkylsilyl group. Some of the bromo- or iodofluoroindoles (26 and 27) were successfully subjected to a basicity gradient-driven selective migration of the heavy halogen. An unexpected finding on the way to the target compounds were the rigorously site-selective metalation of the 5-fluoro-N-(trialkylsilyl)indole (14b; exclusive deprotonation of the 4-position). The fluoroindoles 13-16, although previously known, were accessed more conveniently from suitably substituted nitrobenzenes using the Bartoli or the Leimgruber-Batcho method. A new and very attractive indole synthesis was elaborated consisting of the ortho-lithiation of an N-acyl-protected aniline followed by ortho-formylation, Wittig chloromethylenation and base-catalyzed cyclization accompanied by dehydrochlorination. These five consecutive steps can be contracted to a convenient one-pot protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

AROMATIC AMIDES AS INHIBITORS OF C-FMS KINASE

The invention relates to compounds of Formula (I), wherein A, X, R2 and W are set forth in the specification, as well as solvates, hydrates, tautomers and pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase. Methods of treating autoimmune diseases; and diseases with an inflammatory component; treating metastasis from ovarian cancer, uterine cancer, breast cancer, colon cancer, stomach cancer, hairy cell leukemia and non-small lung carcinoma; and treating pain, including skeletal pain caused by tumor metastasis or osteoarthritis, or visceral, inflammatory, and neurogenic pain; as well as osteoporosis, Paget's disease, and other diseases in which bone resorption mediates morbidity including arthritis, prosthesis failure, osteolytic sarcoma, myeloma, and tumor metastasis to bone with the compounds of Formula (I), are also provided.