89365-48-0

Usage

Appearance

Yellow crystalline solid

Usage

Intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds

Classification

Nitrobenzene derivative

Structure

Contains three bromine atoms and one nitro group attached to a benzene ring

Solubility

Insoluble in water, soluble in organic solvents (e.g., acetone and ethanol)

Application

Primarily used in industrial chemical processes and research laboratories

Safety

Toxic, may cause skin and eye irritation, should be handled with care

Upstream product

• 58683-70-8 1,2,4-tribromo-5-isopropyl-benzene 
• 615-54-3 1,2,4-tribromobenzene 
• 98-82-8 Isopropylbenzene 
• 3638-73-1 2,5-dibromoaniline 
• 108-36-1 1,3-dibromobenzene 
• 5411-50-7 3,4-dibromonitrobenzene 
• 615-57-6 2,4-dibromo-aniline 
• 51686-78-3 2,4-dibromonitrobenzene 
• 615-55-4 3,4-dibromoaniline 

Downstream Products

• 636-28-2 1,2,4,5-tetrabromobenzene 
• 615-86-1 2,4,5-tribromoaniline 
• 75293-97-9 2-nitro-4,5-dibromoaniline 
• 1616359-53-5 C₁₅H₁₉Br₂N₃O₄ 
• 1616359-55-7 C₉H₁₀Br₂N₂O₂ 
• 1616359-50-2 4,5-dibromo-1-N-(propan-2-yl)benzene-1,2-diamine 
• 1616359-34-2 C₉H₁₀Br₂N₂O₃ 
• 265662-25-7 isobutyl-{2-nitro-4,5-bis-[(triisopropylsilanyl)-ethynyl]-phenyl}-amine 
• 649763-38-2 2-amino-4,5-dibromo-N⁽¹⁾-isobutylaniline 
• 265662-22-4 4,5-dibromo-N-isobutyl-2-nitroaniline 

Relevant academic research and scientific papers

Model Systems for Flavoenzyme Activity: Relationships between Cofactor Structure, Binding and Redox Properties

A series of flavins were synthesized bearing electron-withdrawing and -donating substituents. The electrochemical properties of these flavins in a nonpolar solvent were determined. The recognition of these flavins by a diamidopyridine (DAP) receptor and the effect this receptor has on flavin redox potential was also quantified. It was found that the DAP-flavin binding affinity and the reduction potentials (E1/2) for both the DAP-bound and unbound flavins correlated well with functions derived from linear free energy relationships (LFERs). These results provide insight and predictive capability for the interplay of electronics and redox state-specific interactions for both abiotic and enzymatic systems.

Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah receptor mediated pathway

Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyre-sorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10-2-10-5 times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition sequence.

Synthesis and redox properties of novel alkynyl flavins

The synthesis of C7 and/or C8 alkynyl flavins is described. The yields range from 14-48% over six steps. The reduction potentials of these compounds are in good agreement with the values expected based on the Hammett substituent coefficients. (C) 2000 Els