113269-07-1

Basic information

• Product Name: 4-BroMo-5-nitrobenzene-1,2-diaMine
• Synonyms: 4-BroMo-5-nitrobenzene-1,2-diaMine
• CAS NO: 113269-07-1
• Molecular Formula: C₆H₆BrN₃O₂
• Molecular Weight: 232.03474
• Mol File: 113269-07-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 394.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.901±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.46±0.10(Predicted)
• CAS DataBase Reference: 4-BroMo-5-nitrobenzene-1,2-diaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BroMo-5-nitrobenzene-1,2-diaMine(113269-07-1)
• EPA Substance Registry System: 4-BroMo-5-nitrobenzene-1,2-diaMine(113269-07-1)

Safety Data

• Hazardous Substances Data: 113269-07-1(Hazardous Substances Data)

Upstream product

• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 113269-05-9 N,N'-(4-bromo-5-nitro-1,2-phenylene)bis-4-methylbenzenesulfonamide 
• 78680-93-0 N,N'-(4-bromo-1,2-phenylene)bis(4-methylbenzenesulfonamide) 
• 875-51-4 4-Bromo-2-nitroaniline 

Downstream Products

• 113269-09-3 7-bromo-6-nitroquinoxaline 

Relevant articles and documents

Fragment Screening Hit Draws Attention to a Novel Transient Pocket Adjacent to the Recognition Site of the tRNA-Modifying Enzyme TGT

Fragment-based lead discovery was applied to tRNA-guanine transglycosylase, an enzyme modifying post-transcriptionally tRNAs in Shigella, the causative agent of shigellosis. TGT inhibition prevents translation of Shigella's virulence factor VirF, hence reducing pathogenicity. One discovered fragment opens a transient subpocket in the preQ1-recognition site by pushing back an aspartate residue. This step is associated with reorganization of further amino acids structurally transforming a loop adjacent to the recognition site by duplicating the volume of the preQ1-recognition pocket. We synthesized 6-carboxamido-, 6-hydrazido-, and 4-guanidino-benzimidazoles to target the opened pocket, including a dihydro-imidazoquinazoline with a propyn-1-yl exit vector pointing into the transient pocket and displacing a conserved water network. MD simulations and hydration-site analysis suggest water displacement to contribute favorably to ligand binding. A cysteine residue, exclusively present in bacterial TGTs, serves as gatekeeper of the transient subpocket. It becomes accessible upon pocket opening for selective covalent attachment of electrophilic ligands in eubacterial TGTs.

THE FOUR 6-HALO-7-NITROQUINOXALINES

The study of relative nucleofugicities of nitro and halogen in quinoxalines required the synthesis of the four 6-halo-7-nitroquinoxalines 2a-d.The fluoro-, chloro- and bromo-derivatives were made from the commercially available or readily accessible 1,2-diamino-4-halobenzenes, using the nitration of the corresponding p-toluenesulfonamides.This scheme failed in the case of the iodo compound because of extensive nitro-deiodination.The synthesis of 6-iodo-7-nitroquinoxaline was finally achieved from m-fluoroiodobenzene by taking advantage of the high reactivity of fluorine, compared to iodine, in 2,4-dinitrohalobenzenes.