1003-98-1

Basic information

• Product Name: 2-Bromo-4-fluoroaniline
• Synonyms: 4-FLUORO-2-BROMOANILINE;2-BROMO-4-FLUORO-PHENYLAMINE;2-BROMO-4-FLUOROANILINE;Bromofluoroaniline1;2-Bromo-4-fluoroaniline 99%;2-Bromo-4-fluoroaniline99%;2-BROMO-4-FLUOROANILINE 98+%;Benzenamine, 2-bromo-4-fluoro-
• CAS NO: 1003-98-1
• Molecular Formula: C₆H₅BrFN
• Molecular Weight: 190.01
• EINECS: -0
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Fluorobenzene;Miscellaneous;Anilines, Amides & Amines;Bromine Compounds;Fluorine Compounds;Amines;C2 to C6;Nitrogen Compounds;amine| alkyl Fluorine| alkyl bromide;Pyridines
• Mol File: 1003-98-1.mol

Chemical Properties

• Melting Point: 41
• Boiling Point: 221 °C(lit.)
• Flash Point: 220 °F
• Appearance: Clear yellow-brown/Liquid
• Density: 1.67 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0743mmHg at 25°C
• Refractive Index: n20/D 1.583(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.60±0.10(Predicted)
• BRN: 2802562
• CAS DataBase Reference: 2-Bromo-4-fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-fluoroaniline(1003-98-1)
• EPA Substance Registry System: 2-Bromo-4-fluoroaniline(1003-98-1)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1003-98-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-fluoroaniline is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique structure with both bromine and fluorine atoms makes it a valuable building block for creating new drugs with specific properties and functions.
Used in Chemical Synthesis:
2-Bromo-4-fluoroaniline is used as a starting material for the production of various organic compounds. Its aryl fluorinated nature allows for further chemical reactions and modifications, leading to the development of new molecules with potential applications in different industries.
Used in Research and Development:
2-Bromo-4-fluoroaniline is used as a research compound in the field of organic chemistry and medicinal chemistry. It serves as a model compound to study the effects of bromine and fluorine substitution on the properties and reactivity of aniline derivatives, which can provide insights into the design of new molecules with desired characteristics.

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

Upstream product

• 351-83-7 4'-fluoroacetanilide 
• 371-40-4 4-fluoroaniline 
• 1009-22-9 N-(2-bromo-4-fluorophenyl)acetamide 
• 90493-85-9 N-(2-bromophenyl)-N-hydroxyacetamide 

Downstream Products

• 91524-70-8 2-bromo-4-fluoro-1-(methylsulfanyl)benzene 
• 98120-28-6 4-(N,N-dimethylaminophenyl)-(4'-fluoro-2'-bromo)azomethine 
• 700-36-7 2-bromo-4-fluoronitrobenzene 
• 166818-87-7 (2-amino-5-fluorophenyl)phosphonate de diethyle 
• 371-40-4 4-fluoroaniline 
• 625091-78-3 N-(2-bromo-4-fluorophenyl)-4-methylbenzenesulfonamide 
• 1027046-05-4 3-benzo[1,3]dioxol-5-yl-N-(2-bromo-4-fluoro-phenyl)-acrylamide 
• 880384-48-5 C₁₆H₂₁BrFNO₄ 
• 393509-21-2 ethyl (7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate 
• 852102-03-5 N-(2-bromo-4-fluorophenyl)-2,2-diethylbut-3-enamide 
• 13294-75-2 N-(2-bromo-4-fluorophenyl)-benzamide 

Relevant articles and documents

Synthesis of 6-carboxylated phenanthridines by oxidative alkoxycarbonylation-cyclization of 2-isocyanobiphenyls with carbazates

An iron-catalyzed synthesis of 6-carboxylated phenanthridines starting with readily prepared isocyanides and carbazates was developed. Reactions occurred via addition of alkoxycarbonyl radicals to the isocyanide group and subsequent intramolecular cyclization.

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.

Mild and regioselective oxidative bromination of anilines using potassium bromide and sodium perborate

The selective monobromination of various deactivated anilines using potassium bromide and sodium perborate as oxidant has been achieved. The use of ammonium molybdate as catalyst accelerates the rate of reaction but is not essential to obtain good yields and high selectivities. (C) 2000 Elsevier Science Ltd.

Antimicrobial and KPC/AmpC inhibitory activity of functionalized benzosiloxaboroles

A series of 22 benzosiloxaboroles, silicon analogues of strong antimicrobial agents - benzoxaboroles, have been synthesized and tested against β-lactamases KPC- and pAmpC-producing strains of Gram-negative rods. Comprehensive structural-property relationship studies supported by molecular modelling as well as biological studies reveal that 6-B(OH)2-substituted derivative 27 strongly inhibits the activity of cephalosporinases (chromosomally encoded AmpC and plasmid encoded CMY-2) and KPC carbapenemases. It also shows strong ability to inhibit growth of the strains producing KPC-3 when combined with meropenem. In addition, halogen-substituted (mono-, di- or tetra-) benzosiloxaboroles demonstrate high antifungal activity (MIC 1.56–6.25 mg/L) against C. tropicalis, C. guilliermondii and S. cerevisiae. The highest activity against pathogenic yeasts (C. albicans, C. krusei and C. parapsilosis - MICs 12.5 mg/L) and against Gram-positive cocci (S. aureus and E. faecalis - 6.25 mg/L and 25 mg/L respectively) was displayed by 6,7-dichloro-substituted benzosiloxaborole. The studied systems exhibit low cytotoxity toward human lung fibroblasts.

Selective Thiocyanation and Aromatic Amination to Achieve Organized Annulation of Enaminone with Thiocyanate

A tandem insertion of thiocyanate to enamine was performed for the regioselective synthesis of multisubstituted benzoimidazo[2,1-b]thiazoles. This method was shown to be effective in addressing the issue of isomerization encountered in common strategies. With a change made to the leading group on the aniline fragment of enamine, the reaction achieved different transformations, thus enabling multisubstituted benzo[4,5]imidazo[2,1-b]thiazoles and thiazoles in satisfactory yields.

4 - Fluorine substituted aryl amine compound and synthesis method thereof

The invention discloses a synthesis method of 4 -fluorine substituted aryl amine compound, which comprises the following steps: 1) taking acyl-protected phenylhydroxylamine as a substrate, and generating 4 -fluorine substituted aniline compound under basic conditions by taking sulfonyl fluoride as a fluorine source in a polar solvent. 2) The deprotection is carried out under dilute acid conditions or Pd by catalytic hydrogenation to give the 4 - fluorine-substituted aryl amine compound. 4 - Fluorine substituted aniline compounds which are synthesized by the invention greatly increase the lipophilic property due to the introduction of fluorine atoms, and can be widely applied to preparation of fluorine-containing drugs and pesticide and dye intermediates. , The adopted raw materials are industrial products, are cheap and easily available, and are commercially available. 4 - Fluoroaryl aniline prepared by the method is high in yield, and the product with the purity 90% can be obtained in a yield of more than ≥ 99%. The method is simple to operate and low in cost, is very suitable for industrialization, and can be widely popularized and used.

Nitromethane as a reagent for the synthesis of 3-nitroindoles from 2-haloarylamine derivatives

A new approach to the synthesis of 3-nitroindoles using palladium-catalyzed arylation of nitromethane with N-(2-bromoaryl)imidates was developed. A convenient and rapid method for cyclization of ethyl N-(2-nitromethylaryl)acetimidates to 2-methyl-3-nitro-1H-indoles was proposed.

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.

Preparation method of 3-bromo-4-bromonitrophenol

The invention discloses an industrial preparation method of 3-bromo-4-bromonitrophenol. According to the industrial preparation method of the 3-bromo-4-bromonitrophenol, p-fluoroaniline serves as an initial raw material, and the 3-bromo-4-bromonitrophenol

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.