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

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

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

Upstream product

• 5411-50-7 3,4-dibromonitrobenzene 
• 26429-41-4 1,2-dibromo-3-nitrobenzene 
• 591-19-5 m-Bromoaniline 
• 583-53-9 2,3-dibromobenzene 
• 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 

Downstream Products

• 121866-29-3 1-(2-bromo-3-aminophenyl)heptyne 
• 126190-14-5 2,3-Dibromothiophenol 
• 126190-13-4 Dithiocarbonic acid S-(2,3-dibromo-phenyl) ester O-ethyl ester 
• 15437-36-2 N-(2,3-Dibromphenyl)anthranilsaeure 
• 591-19-5 m-Bromoaniline 
• 823-54-1 3-bromo-4-chloroaniline 
• 615-55-4 3,4-dibromoaniline 
• 642-95-5 2,3,4-tribromoaniline 
• 145142-28-5 4-Amino-2,3-dibromobenzaldehyde 
• 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 

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.

Synthesis and biological evaluation of piperazinyl heterocyclic antagonists of the gonadotropin releasing hormone (GnRH) receptor

Antagonism of the gonadotropin releasing hormone (GnRH) receptor has resulted in positive clinical results in reproductive tissue disorders such as endometriosis and prostate cancer. Following the recent discovery of orally active GnRH antagonists based on a 4-piperazinylbenzimidazole template, we sought to investigate the properties of heterocyclic isosteres of the benzimidazole template. We report here the synthesis and biological activity of eight novel scaffolds, including imidazopyridines, benzothiazoles and benzoxazoles. The 2-(4-tert-butylphenyl)-8-(piperazin-1-yl)imidazo[1,2-a]pyridine ring system was shown to have nanomolar binding potency at the human and rat GnRH receptors as well as functional antagonism in vitro. Additional structure-activity relationships within this series are reported along with a pharmacokinetic comparison to the benzimidazole-based lead molecule.

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.

Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor

The present invention relates to Gonadotropin Releasing Hormone (GnRH, also known as Luteinizing Hormone Releasing Hormone) receptor antagonists.

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.

Copper(I)-Induced Bromo-Hydrogen Exchange of 2,3-Dibromoanilines

The copper(I)-induced bromine-hydrogen exchange reaction of 2,3-dibromoaniline and 5-substituted 2,3-dibromoanilines in the 2-position has been kinetically studied in water-acetic acid-hydrochloric acid medium at 90 deg C.The dehalogenation reaction is of second order, first order in both substrate and Cu+, and may be interpreted as a reductive substitution, composed of two one-electron steps.The 2,3-dibromophenol was only qualitatively investigated, but gave similar results.

4 AND 5-Halo substituted 2-indanamine compounds

2-Indanamine compounds having 4 and 5-halo substituents are inhibitors of phenylethanolamine N-methyltransferase.