615-55-4

Basic information

• Product Name: 3,4-DIBROMOANILINE
• Synonyms: Benzenamine, 3,4-dibromo-;3,4-DIBROMOANILINE
• CAS NO: 615-55-4
• Molecular Formula: C₆H₅Br₂N
• Molecular Weight: 250.9186
• EINECS: 210-158-4
• Mol File: 615-55-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 80.5°C
• Boiling Point: 100°C (rough estimate)
• Flash Point: 128.1°C
• Appearance: /
• Density: 1.9318 (rough estimate)
• Vapor Pressure: 0.00236mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• PKA: 2.82±0.10(Predicted)
• CAS DataBase Reference: 3,4-DIBROMOANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIBROMOANILINE(615-55-4)
• EPA Substance Registry System: 3,4-DIBROMOANILINE(615-55-4)

Safety Data

• Hazardous Substances Data: 615-55-4(Hazardous Substances Data)

Usage

Description

3,4-Dibromoaniline is an organic compound with the chemical formula C6H4Br2NH2, featuring two bromine atoms attached to the benzene ring at the 3 and 4 positions, and an amino group (-NH2) attached to the remaining carbon. It is a significant intermediate in the synthesis of various organic compounds and has unique chemical properties due to the presence of both bromine atoms and the amino group.

Uses

Used in Pharmaceutical Industry:
3,4-Dibromoaniline is used as a key intermediate in the synthesis of pharmaceutical compounds, particularly those with potential therapeutic applications. Its unique structure allows for further chemical modifications, making it a versatile building block for the development of new drugs.
Used in Chemical Synthesis:
3,4-Dibromoaniline is used as a valuable precursor in organic synthesis, especially in reactions involving the formation of benzynes. Benzynes are reactive intermediates that can undergo various types of chemical reactions, such as cyclization, substitution, and addition, leading to the formation of complex organic molecules with potential applications in various industries.
Used in Dye Manufacturing:
3,4-Dibromoaniline can be used as a starting material for the production of dyes, particularly those with specific color properties. The presence of bromine atoms and the amino group in its structure allows for the creation of dyes with unique characteristics, making it a useful compound in the dye manufacturing process.
Used in Polymer Industry:
3,4-Dibromoaniline can be utilized in the polymer industry as a monomer for the synthesis of polymers with specific properties. The bromine atoms in its structure can be used to introduce cross-linking or other functional groups, leading to the development of polymers with tailored characteristics for various applications.

InChI:InChI=1/C6H5Br2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2

Upstream product

• 591-19-5 m-Bromoaniline 
• 7647-01-0 hydrogenchloride 
• 621-38-5 3-bromoacetanilide 
• 5411-50-7 3,4-dibromonitrobenzene 
• 26429-41-4 1,2-dibromo-3-nitrobenzene 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 586-78-7 para-nitrophenyl bromide 
• 13296-94-1 2-bromo-4-nitroaniline 
• 583-53-9 2,3-dibromobenzene 
• 140-89-6 potassium ethyl xanthogenate 
• 615-54-3 1,2,4-tribromobenzene 
• 7664-41-7 ammonia 
• 106-40-1 4-bromo-aniline 
• 62-53-3 aniline 

Downstream Products

• 119043-66-2 N,N'-bis-(3,4-dibromo-phenyl)-thiourea 
• 2369-37-1 1,2,-dibromo-4-fluorobenzene 
• 60956-24-3 1,2-dibromo-4-chlorobenzene 
• 615-54-3 1,2,4-tribromobenzene 
• 615-56-5 3,4-dibromophenol 
• 60469-89-8 4-dimethylamino-o-dibromobenzene 
• 67450-65-1 N-(3,4-Dibromo-phenyl)-N-((1R,2R)-2-dimethylamino-cyclopentyl)-propionamide 
• 23747-86-6 1-(3,4-Dibromo-phenyl)-3-(4-trifluoromethyl-phenyl)-urea 
• 121866-24-8 1-(2-bromo-5-aminophenyl)heptyne 
• 123994-76-3 2-(3,4-Dibromo-phenylamino)-1,9-dihydro-purin-6-one 
• 126190-11-2 O-Ethyl S-(3,4-dibromophenyl)xanthate 
• 137840-21-2 2-[(3,4-Dibromo-phenylcarbamoyl)-methyl]-benzoic acid 
• 24108-97-2 3,4-dibromoacetanilide 
• 60108-72-7 1,2-dibromo-4-biphenyl 

Relevant articles and documents

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.

Electrophilic bromination of meta-substituted anilines with N-bromosuccinimide: Regioselectivity and solvent effect

N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-with-drawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium. Georg Thieme Verlag Stuttgart.

7′-Substituted benzothiazolothio- and pyridinothiazolothio-purines as potent heat shock protein 90 inhibitors

We report on the discovery of benzo- and pyridinothiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7′-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chloro-benzothiazol-2-ylsulfanyl)-9-(2-cyclopropylamino-ethyl) -9H-purin-6-ylamine).