147021-89-4

Basic information

• Product Name: 4-Bromo-3-nitrobenzene-1,2-diamine
• Synonyms: 4-Bromo-3-nitrobenzene-1,2-diamine;4-Bromo-3-nitro-1,2-benzenediamine;1,2-Benzenediamine,4-bromo-3-nitro-
• CAS NO: 147021-89-4
• Molecular Formula: C₆H₆BrN₃O₂
• Molecular Weight: 232.04
• Mol File: 147021-89-4.mol

Chemical Properties

• Boiling Point: 352.4 °C at 760mmHg
• Flash Point: 166.9 °C
• Appearance: /
• Density: 1.901 g/cm³
• Vapor Pressure: 3.86E-05mmHg at 25°C
• Refractive Index: 1.735
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 4-Bromo-3-nitrobenzene-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3-nitrobenzene-1,2-diamine(147021-89-4)
• EPA Substance Registry System: 4-Bromo-3-nitrobenzene-1,2-diamine(147021-89-4)

Safety Data

• Hazardous Substances Data: 147021-89-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Bromo-3-nitrobenzene-1,2-diamine is used as a building block for the synthesis of other organic compounds. Its presence of amine and halogen groups allows for versatile chemical reactions, making it a valuable intermediate in the creation of new materials and compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-Bromo-3-nitrobenzene-1,2-diamine is utilized as a key component in the development of new drugs. Its unique structure and reactivity enable the design of novel therapeutic agents with potential applications in medicine.
Used in Dye Industry:
4-Bromo-3-nitrobenzene-1,2-diamine is employed as a precursor in the production of dyes. Its chemical properties allow for the creation of dyes with specific characteristics, such as color intensity and stability, which are important for various applications.
Used in Research and Development:
Due to its unique structure and properties, 4-Bromo-3-nitrobenzene-1,2-diamine is also used in scientific research and development. It serves as a valuable tool for exploring new chemical reactions and understanding the behavior of different functional groups in various chemical systems.
Potential Applications in Medicine and Biotechnology:
4-Bromo-3-nitrobenzene-1,2-diamine may have potential applications in the fields of medicine and biotechnology. Its unique structure could be harnessed to develop new therapeutic agents or diagnostic tools, contributing to advancements in healthcare and biotechnological applications.

InChI:InChI=1/C6H6BrN3O2/c7-3-1-2-4(8)5(9)6(3)10(11)12/h1-2H,8-9H2

Upstream product

• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 5228-61-5 5-bromo-2-nitroaniline 
• 1753-19-1 5-bromobenzo[c][1,2,5]selenadiazole 
• 1753-20-4 5-bromo-4-nitrobenzo-2,1,3-selenadiazole 

Relevant articles and documents

Synthesis and structure-activity relationships of substituted 1,4- dihydroquinoxaline-2,3-diones: Antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors

A series of mono-, di-, tri-, and tetrasubstituted 1,4- dihydroquinoxaline-2,3-diones (QXs) were synthesized and evaluated as antagonists at N-methyl-D-aspartate (NMDA)/glycine sites and α-amino-3- hydroxy-5-methylisoxazole-4-propionic acid-preferring non-NMDA receptors. Antagonist potencies were measured by electrical assays in Xenopus oocytes expressing rat whole brain poly(A)+ RNA. Trisubstituted QXs 17a (ACEA 1021), 17b (ACEA 1031), 24a, and 27, containing a nitro group in the 5 position and halogen in the 6 and 7 positions, displayed high potency (K(b) ~ 6-8 nM) at the glycine site, moderate potency at non-NMDA receptors (K(b) = 0.9-1.5 μM), and the highest (120-250-fold) selectivity in favor of glycine site antagonism over non-NMDA receptors. Tetrasubstituted QXs 17d,e were more than 100-fold weaker glycine site antagonists than the corresponding trisubstituted QXs with F being better tolerated than Cl as a substituent at the 8 position. Di- and monosubstituted QXs showed progressively weaker antagonism compared to trisubstituted analogues. For example, removal of the 5-nitro group of 17a results in a ~100-fold decrease in potency (10a,b,z), while removal of both halogens from 17a results in a ~3000-fold decrease in potency (10v). In terms of steady-state inhibition, most QX substitution patterns favor antagonism at NMDA/glycine sites over antagonism at non-NMDA receptors. Among the QXs tested, only 17i was slightly selective for non- NMDA receptors.

A useful methodology for the synthesis of 2-methyl-4-nitrobenzimidazoles

Cyclocondensation of 3-nitro-1,2-benzenediamines 2 with 2,4-pentanedione provides a convenient route for the preparation of 2-methyl-4-nitrobenzimidazoles 3. A discrepancy in the literature regarding the 5-chloro-, 5-methoxy- and 5-methyl derivatives of the title compounds is discussed.