608-22-0

Basic information

• Product Name: 2,3-Dibromoaniline
• Synonyms: 2,3-Dibromoaniline
• CAS NO: 608-22-0
• Molecular Formula: C₆H₅Br₂N
• Molecular Weight: 250.9186
• Mol File: 608-22-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 41-43 °C
• Boiling Point: 289.331°C at 760 mmHg
• Flash Point: 128.783°C
• Appearance: /
• Density: 2.022g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 1.46±0.10(Predicted)
• CAS DataBase Reference: 2,3-Dibromoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dibromoaniline(608-22-0)
• EPA Substance Registry System: 2,3-Dibromoaniline(608-22-0)

Safety Data

• Hazardous Substances Data: 608-22-0(Hazardous Substances Data)

Usage

Uses

2,3-Dibromoaniline is a useful reactant in organic synthesis.

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

Upstream product

• 591-19-5 m-Bromoaniline 
• 57383-80-9 2,3-dibromophenol 
• 1287791-78-9 N-(2,3-dibromophenyl)-2-hydroxy-2-methylpropanamide 
• 1287791-69-8 2-(2,3-dibromophenoxy)-2-methylpropanamide 
• 863870-80-8 O-2,3-dibromophenyl N,N-diethylcarbamate 
• 863870-72-8 O-3-bromophenyl N,N-diethylcarbamate 
• 583-53-9 2,3-dibromobenzene 
• 5411-50-7 3,4-dibromonitrobenzene 
• 26429-41-4 1,2-dibromo-3-nitrobenzene 

Downstream Products

• 915135-34-1 4-tert-butyl-N-(2,3-dibromophenyl)benzamide 
• 126189-99-9 S-(2,3-Dibromophenyl)mercapturic acid 
• 121866-30-6 1-(2-bromo-3-acetamidophenyl)heptyne 
• 121866-27-1 m-n-heptylacetanilide 
• 121866-26-0 3-heptylphenylamine 
• 156498-30-5 Furan-2-carboxylic acid (2,3-dibromo-phenyl)-methyl-amide 
• 957055-24-2 C₁₉H₁₅NO 
• 957055-33-3 6,7-dibromo-1-methyl-3-phenyl-1H-indole 
• 957055-21-9 6,7-dibromo-3-phenyl-1H-indole 
• 121866-28-2 1,2-dibromo-3-acetamidobenzene 
• 145142-28-5 4-Amino-2,3-dibromobenzaldehyde 
• 642-95-5 2,3,4-tribromoaniline 
• 591-19-5 m-Bromoaniline 
• 823-54-1 3-bromo-4-chloroaniline 

Relevant articles and documents

Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1 H-indoles

2,3-Dihaloanilines have been proved as useful starting materials for synthesizing 4-halo-1H-indoles. Subsequent or in situ functionalization of the prepared haloindoles allows the access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles in good overall yields. As no efficient synthetic routes to 2,3-dihaloanilines have been described in the literature, different approaches to the preparation of these 1,2,3-functionalized aromatic precursors are now presented. The most general one involves a Smiles rearrangement from the corresponding 2,3-dihalophenols and allows the preparation of 2,3-dihaloanilides in a straightforward and synthetically useful manner.

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.

Rates and Regioselectivities of the Palladium-Catalyzed Ethynylation of Substituted Bromo- and Dibromobenzenes

The Pd(0)/Cu2Br2-catalyzed ethynylation of 1,2-dibromo-4-nitro- and 1,2-dibromo-3-nitrobenzenes provide rapidly the product in which the bromine para or ortho to the nitro group is displaced, whereas the corresponding dibromoacetamidobenzenes provide the product of meta displacement slowly.Investigation of the rates of a series of para-substituted bromobenzenes indicates that the reaction is zero-order with respect to the heptyne and bromobenzene concentration, with a Hammett ρ value of 2.8.