367-24-8

Basic information

• Product Name: 4-Bromo-2-fluoroaniline
• Synonyms: Benzenamine, 4-bromo-2-fluoro-;AKOS BBS-00003609;4-BROMO-2-FLUORO-PHENYLAMINE;4-BROMO-2-FLUOROANILINE;2-Fluoro-4-Bromoaniline;Bromofluoroaniline4;-BROMO-2-FLUOROANILINE, 98%;4-Bromo-2-fluoroaniline,98+%
• CAS NO: 367-24-8
• Molecular Formula: C₆H₅BrFN
• Molecular Weight: 190.01
• EINECS: 206-685-4
• Product Categories: Trifluoromethoxybenzene Series;Fluorobenzene;Fluoro-Aromatics;PHARMACEUTICAL INTERMEDIATES;Anilines, Aromatic Amines and Nitro Compounds;Aniline;Benzenes;Anilines, Amides & Amines;Bromine Compounds;Fluorine Compounds;Amines;C2 to C6;Nitrogen Compounds;amine| alkyl Fluorine| alkyl bromide
• Mol File: 367-24-8.mol

Chemical Properties

• Melting Point: 40-42 °C
• Boiling Point: 103-108 °C (13 mmHg)
• Flash Point: 220 °F
• Appearance: Beige to light brown to brown-gray or gray/Crystalline Mass, Powder, Crystals and/or Chunks
• Density: 1.6196 (rough estimate)
• Vapor Pressure: 1.62mmHg at 25°C
• Refractive Index: 1.4710 (estimate)
• Storage Temp.: Room temperature.
• PKA: 2.50±0.10(Predicted)
• Stability: Stable. Incompatible with acid chlorides, acid anhydrides, strong acids, strong oxidizing agents.
• BRN: 2081089
• CAS DataBase Reference: 4-Bromo-2-fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-fluoroaniline(367-24-8)
• EPA Substance Registry System: 4-Bromo-2-fluoroaniline(367-24-8)

Safety Data

• Hazard Codes: Xi,T,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39-36
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 367-24-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Bromo-2-fluoroaniline is used as an organic synthesis intermediate due to its unique structure, which allows for further chemical reactions to produce a variety of compounds. Its application in this field is crucial for the development of new organic molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Bromo-2-fluoroaniline serves as a key intermediate in the synthesis of various drugs. Its role in the development of new medications is significant, as it can be used to create molecules with specific therapeutic properties.
Used in Laboratory Research and Development:
4-Bromo-2-fluoroaniline is also utilized in laboratory research and development processes. It is an essential compound for scientists to study and understand the behavior of different chemical reactions, which can lead to the discovery of new chemical entities and advancements in the field of chemistry.
Used in Chemical Production Processes:
Furthermore, 4-Bromo-2-fluoroaniline is employed in chemical production processes, where it is used to manufacture various chemicals and materials. Its versatility and reactivity make it a valuable component in the chemical industry.
Used in Synthesis of 4-amino-3-fluorophenyl boronic acid:
4-Bromo-2-fluoroaniline has been specifically used in the synthesis of 4-amino-3-fluorophenyl boronic acid, which is an important compound in the field of materials science and pharmaceuticals.
Used in Chemical Modification and Synthesis of Boronic Acid Derivatives:
Additionally, 4-Bromo-2-fluoroaniline is utilized in the chemical modification and synthesis of boronic acid derivatives for ultraviolet-visible titration. This application highlights its importance in analytical chemistry and the development of new methods for chemical analysis.

Synthesis

To a stirred solution of 4-bromo-2-fluoro-l -nitrobenzene (10 g, 45.5 mmol) in EtOH (50 mL)AVater (20 mL) was added iron (12.7 g, 230 mmol) and NH4C1 (24.3 g, 455 mmol). The reaction mixture was stirred at 90 °C for 2 h. After 2 h the reaction mixture was filtered over Celite. The filter cake was washed with EtOH (300 mL), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (S1O2, Petroleum ether/EtOAc=10: l to 5: 1) to afford 4-bromo-2-fluoroaniline.

InChI:InChI:1S/C6H5BrFN/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

Upstream product

• 348-54-9 2-Fluoroaniline 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 106-40-1 4-bromo-aniline 
• 1601-98-5 1,2-bis(4-bromophenyl)diazene 

Downstream Products

• 71417-01-1 2-(4-bromo-2-fluorophenylaminocarbonyl)-1-cyclohexene-1-carboxylic acid 
• 129367-47-1 (4-Bromo-2-fluoro-phenyl)-methoxymethyl-amine 
• 105942-08-3 4-bromo-6-fluorobenzonitrile 
• 86156-95-8 2-amino-5-bromo-3-fluorobenzenesulphonic acid 
• 165180-44-9 N-(4-bromo-2-fluorophenyl)pivalamide 
• 213190-12-6 4-bromo-2-fluoro-N-methylaniline 
• 213190-13-7 (4-bromo-2-fluorophenyl)ethylamine 
• 213190-14-8 (4-bromo-2-fluorophenyl)hexylamine 
• 348-54-9 2-Fluoroaniline 
• 42822-57-1 diethyl (4-aminophenyl)phosphonate 
• 166818-87-7 (2-amino-5-fluorophenyl)phosphonate de diethyle 
• 768350-54-5 7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine hydrochloride 
• 893734-49-1 3-fluoro-4′-methoxybiphenyl-4-amine 
• 299440-17-8 (4-bromo-2-fluorobenzene)hydrazine 

Relevant articles and documents

A Practical Procedure for Regioselective Bromination of Anilines

A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

Synthesis of 2 - fluoro aniline compounds of the method

The invention discloses a method for synthesizing 2 - fluoro aniline compounds of the method, the method is: shown in formula Ia aniline compound of formula Ib α and β shown aniline compound as raw materials, through coupling reaction shown [...] azobenzene compound II, then the type II shown azobenzene compound with a palladium catalyst, fluorination reagent, additive, organic solvent, in the 30 - 150 °C temperature closed agitating the fluorination reaction, [...] compound of formula III, type III compounds are shown in the reaction under the action of a reducing [...] shown IV 2 - fluoro aniline compounds; this invention synthetic 2 - fluoro aniline compounds substrate wide adaptability, mild reaction conditions, the operation is simple, fluorinated and good selectivity, [...] aniline compounds is prepared by many drug molecule is an important intermediate and starting material, wide application prospects.

Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination

A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.

NOVEL SUBSTITUTED CYCLOBUTYLBENZENE COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS

Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof: (Formula (I)). Also disclosed herein are uses of a compound disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of a composition in the potential treatment or prevention of an IDO-associated disease or disorder.

Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach

A simple, environmentally benign methodology has been developed to synthesize some bromoorganic compounds which have potential as antimicrobial agents. The required compounds were obtained through microwave (MW) irradiation, on-water reactions and using cetyltrimethylammonium tribromide (CTMATB) as the bromine source. The high yield of the product could be achieved within short reaction times, thus representing the main attribute of the present synthetic approach. The compounds were evaluated for in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Bacillus subtilis. Further, in silico studies were carried out to elucidate the interactions of the compounds with the bacterial proteins.

2-OXO-THIAZOLE DERIVATIVES AS A2A INHIBITORS AND COMPOUNDS FOR USE IN THE TREATMENT OF CANCERS

The present invention relates to compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof. The invention further relates to the use of the compounds of Formula (I) as A2A inhibitors. The invention also relates to the use of the compounds of Formula (I) for the treatment and/or prevention of cancer. The invention also relates to a process for manufacturing compounds of Formula (I).

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.

A 4 - bromo - 2 - fluoro aniline the selective synthesis of the method (by machine translation)

The patented invention has a quaternary ammonium salt produced in situ crosses the bromineneighbouring fluorine aniline production bromide 4 - bromo - 2 - fluoro aniline. Process step its: the quaternary ammonium salt, neighbouring fluorine aniline and solvent are added to a reaction flask, stirring and dissolving, the control temperature is lower than the 30 °C under the condition of, slow instillment bromide, about 30 - 60min drop end, after the temperature of the material to rise to 40 °C left instead on invitation 2.5h; cooling to room temperature, filtered, the filter cake is two times the washing of the solvent, then the filter cake is dispersed in the solvent, then adding 10% of sodium hydroxide solution to pH=7 - 8 and, standing off the aqueous phase, organic uses deionized water to wash two times is to distill the solvent to obtain 4 - bromo - 2 - fluoro aniline. (by machine translation)