6298-38-0

Basic information

• Product Name: 3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE
• Synonyms: 3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE;1,2,4-Benzotriazin-3-aMine, 7-broMo-, 1-oxide;7-bromo-1,2,4-Benzotriazin-3-amine 1-oxide;7-bromo-1-oxido-1,2,4-benzotriazin-1-ium-3-amine
• CAS NO: 6298-38-0
• Molecular Formula: C₇H₅BrN₄O
• Molecular Weight: 241.0448
• Mol File: 6298-38-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 294-295 °C (decomp)
• Boiling Point: 404.5°Cat760mmHg
• Flash Point: 198.4°C
• Appearance: /
• Density: 2.11g/cm³
• Vapor Pressure: 3.16E-08mmHg at 25°C
• Refractive Index: 1.82
• PKA: 3.00±0.50(Predicted)
• CAS DataBase Reference: 3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE(6298-38-0)
• EPA Substance Registry System: 3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE(6298-38-0)

Safety Data

• Hazardous Substances Data: 6298-38-0(Hazardous Substances Data)

Usage

General Description

3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE is a chemical compound with the molecular formula C6H4BrN4O. It is a derivative of benzotriazine and belongs to the class of organic compounds known as benzotriazines. 3-AMINO-7-BROMO-1,2,4-BENZOTRIAZINE-1-OXIDE is a white to off-white crystalline solid and is primarily used in the field of research and development. It is known for its potential as a building block in the synthesis of pharmaceuticals and other organic compounds. Additionally, its unique structure and properties make it a valuable tool for investigating various biochemical processes and pathways. However, due to its chemical nature, it should be handled with care and in accordance with proper safety protocols.

InChI:InChI=1/C7H7BrN4O/c8-4-1-2-5-6(3-4)12(13)11-7(9)10-5/h1-4,13H,(H2,9,11)

Upstream product

• 420-04-2 CYANAMID 
• 875-51-4 4-Bromo-2-nitroaniline 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 113-00-8 guanidine nitrate 
• 119707-95-8 2-nitro-4-bromophenylguanidine 
• 881-50-5 N-(4-bromo-2-nitrophenyl)acetamide 
• 103-88-8 4-bromoacetanilide 
• 5228-61-5 5-bromo-2-nitroaniline 
• 20611-81-8 disodium cyanamide 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 867331-58-6 [7-(2,6-dimethyl-phenyl)-5-nitro-1-oxy-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine 
• 867331-59-7 7-(2,6-dimethyl-phenyl)-N₃-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[1,2,4]triazine-3,5-diamine 
• 867330-99-2 7-(2,6-dimethyl-phenyl)-5-nitro-1-oxy-benzo[1,2,4]triazin-3-ylamine 
• 929194-33-2 7-(2,6-dichloro-phenyl)-benzo[1,2,4]triazin-3-ylamine 
• 677297-90-4 7-(2,6-Dimethyl-phenyl)-benzo[1,2,4]triazin-3-ylamine 

Relevant articles and documents

Organic compound and organic electroluminescent device containing same

The invention relates to an organic compound, which is characterized by having a structure as shown in (1), wherein L1 and L2 are respectively and independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group; Arl and Ar2 are respectively and independently selected from a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; R is halogen, a cyano group, an alkyl group, a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; and n represents an integer of 0-3.

Application of Suzuki–Miyaura and Buchwald–Hartwig Cross-coupling Reactions to the Preparation of Substituted 1,2,4-Benzotriazine 1-Oxides Related to the Antitumor Agent Tirapazamine

Many 1,2,4-benzotriazine 1,4-dioxides display the ability to selectively kill the oxygen-poor cells found in solid tumors. As a result, there is a desire for synthetic routes that afford access to substituted 1,2,4-benzotriazine 1-oxides that can be used as direct precursors in the synthesis of 1,2,4-benzotriazine 1,4-dioxides. Here we describe the use of Suzuki–Miyaura and Buchwald–Hartwig cross-coupling reactions for the construction of various 1,2,4-benzotriazine 1-oxide analogs bearing substituents at the 3-position, 6-position, and 7-position.

Discovery and optimization of benzotriazine Di-N-oxides targeting replicating and nonreplicating mycobacterium tuberculosis

Compounds bactericidal against both replicating and nonreplicating Mtb may shorten the length of TB treatment regimens by eliminating infections more rapidly. Screening of a panel of antimicrobial and anticancer drug classes that are bioreduced into cytotoxic species revealed that 1,2,4-benzotriazine di-N-oxides (BTOs) are potently bactericidal against replicating and nonreplicating Mtb. Medicinal chemistry optimization, guided by semiempirical molecular orbital calculations, identified a new lead compound (20q) from this series with an MIC of 0.31 μg/mL against H37Rv and a cytotoxicity (CC 50) against Vero cells of 25 μg/mL. 20q also had equivalent potency against a panel of single-drug resistant strains of Mtb and remarkably selective activity for Mtb over a panel of other pathogenic bacterial strains. 20q was also negative in a L5178Y MOLY assay, indicating low potential for genetic toxicity. These data along with measurements of the physiochemical properties and pharmacokinetic profile demonstrate that BTOs have the potential to be developed into a new class of antitubercular drugs.