1575-37-7

Usage

Uses

Used in Organic Synthesis:
4-Bromo-1,2-benzenediamine is used as a crucial intermediate in organic synthesis for the production of various chemical compounds and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-Bromo-1,2-benzenediamine serves as an essential raw material for the development of new drugs and medicinal compounds.
Used in Agrochemicals:
4-Bromo-1,2-benzenediamine is utilized as a key component in the formulation of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Dyestuff Industry:
4-Bromo-1,2-benzenediamine is also employed in the dyestuff industry as a vital intermediate for the synthesis of various dyes and pigments.
Used in Fluorescent Materials:
4-Bromo-1,2-benzenediamine can be used as a precursor for preparing fluorescent dipolar quinoxaline derivatives, which have potential applications as emissive and electron-transport materials.
Used in Synthesis of 6-Bromo-2-Methylbenzimidazole:
Additionally, it is used in the synthesis of 6-bromo-2-methylbenzimidazole, a compound with various applications in the chemical and pharmaceutical industries.

InChI:InChI=1/C6H7BrN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 591-19-5 m-Bromoaniline 
• 5228-61-5 5-bromo-2-nitroaniline 
• 36387-84-5 4-bromo-9-oxido-8-oxa-7,9-diazabicyclo[4.3.0]nona-1⁽⁹⁾,2,4,6-tetraene 
• 875-51-4 4-Bromo-2-nitroaniline 
• 51686-78-3 2,4-dibromonitrobenzene 
• 106-40-1 4-bromo-aniline 
• 881-50-5 N-(4-bromo-2-nitrophenyl)acetamide 
• 88-74-4 2-nitro-aniline 
• 54558-18-8 1,2-dinitro-4,5-dibromobenzene 
• 103-88-8 4-bromoacetanilide 

Downstream Products

• 78680-93-0 N,N'-(4-bromo-1,2-phenylene)bis(4-methylbenzenesulfonamide) 
• 229638-10-2 C₄₆H₄₂N₂O₇ 
• 578709-05-4 5-bromo-2-(piperidin-4-yl)-1H-benzo[d]imidazole 
• 405170-93-6 2-nitro-4-thiophen-2-yl-phenylamine 
• 107469-36-3 Toluene-4-sulfonate11-bromo-13-methyl-7-oxo-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-13-ium; 
• 107469-38-5 Toluene-4-sulfonate10-bromo-13-methyl-7-oxo-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-13-ium; 
• 864296-72-0 N'-(2-amino-4-bromo-phenyl)-N-boc-(S)-O-methyl-serinamide 
• 864296-73-1 N'-(2-amino-5-bromo-phenyl)-N-boc-(S)-O-methyl-serinamide 
• 936939-49-0 2-amino-4-(2-methoxypyridin-3-yl)phenylamine 
• 1410014-47-9 C₁₆H₁₅BrN₂O₂ 
• 808127-74-4 5-bromo-N-phenyl-1H-benzo[d]imidazol-2-amine 
• 898825-88-2 7-bromo-2-phenyl-quinoxaline 
• 898825-98-4 6-bromo-2-phenyl-quinoxaline 
• 1276022-77-5 (S)-3-(1H-benzo[d]imidazol-6-yl)-4-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

An improved understanding of the reaction of bis(bromomethyl)quinoxaline 1-N-oxides with amines using substituent effects

(Chemical Equation Presented) The reaction of bis(bromomethyl)quinoxaline N-oxides with amines is interesting from a reaction mechanism perspective and due to the reported biological activity of compounds in this general class. The complex mechanism of th

A novel benzimidazole derivative binds to the DNA minor groove and induces apoptosis in leukemic cells

DNA minor groove binders are an important class of chemotherapeutic agents. These small molecule inhibitors interfere with various cellular processes like DNA replication and transcription. Several benzimidazole derivatives showed affinity towards the DNA

Fluorene- and benzimidazole-based blue light-emitting copolymers: Synthesis, photophysical properties, and PLED applications

Blue light-emitting materials are receiving considerable academic and industrial interest due to their potential applications in optoelectronic devices. In this study, blue light-emitting copolymers based on 9,9'-dioctylfluorene and 2,2'-(1,4-phenylene)-bis(benzimidazole) moieties were synthesized through palladium-catalyzed Suzuki coupling reaction. While the copolymer consisting of unsubstituted benzimidazoles (PFBI0) is insoluble in common organic solvents, its counterpart with N-octyl substituted benzimidazoles (PFBI8) enjoys good solubility in toluene, tetrahydrofuran, dichloromethane (DCM), and chloroform. The PFBI8 copolymer shows good thermal stability, whose glass transition temperature and onset decomposition temperature are 103 and 428 °C, respectively. Its solutions emit blue light efficiently, with the quantum yield up to 99% in chloroform. The electroluminescence (EL) device of PFBI8 with the configuration of indium-tin oxide/poly(ethylenedioxythiophene): poly(styrene sulfonic acid)/PFBI8/1,3,5-tris(1-phenyl-1H-benzimidazole-2-yl) benzene/LiF/Al emits blue light with the maximum at 448 nm. Such unoptimized polymer light-emitting diode (PLED) exhibits a maximum luminance of 1534 cd/m2 with the current efficiency and power efficiency of 0.67 cd/A and 0.20 lm/W, respectively. The efficient blue emission and good EL performance make PFBI8 promising for optoelectronic applications. 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 A conjugated polymer based on 9,9'-dioctylfluorene and N-octyl substituted 2,2'-(1,4-phenylene)- bis(benzimidazole) moieties (PFBI8) was synthesized. Its solutions emit blue light efficiently, with the quantum yield up to 99% in chloroform. It is also morphologically and thermally stable, with glass transition temperature and decomposition temperature as high as 103 and 428 °C, respectively. The polymer light-emitting diode using PFBI8 as the active emitting layer exhibits blue emission (448 nm) with the maximum luminance, current efficiency and power efficiency of 1534 cd/m2, 0.67 cd/A, and 0.20 lm/W, respectively. Copyright

Polymer light-emitting devices based on europium(III) complex with 11-bromo-dipyrido[3,2-a:2′,3′-c]phenazine

Polymer light-emitting diodes (PLEDs) containing Eu(DBM)3(BrDPPz) (DBM is dibenzoylmethane, and BrDPPz is 11-bromo-dipyrido[3,2-a:2′,3′-c]phenazine) doped in a blend of poly(9,9-dioctylfluorene) (PFO) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) as the host matrix are reported. Eu(DBM)3(BrDPPz) exhibited high thermal stability and intense UV-Vis absorption. Narrow-bandwidth red emission at 612 nm with a full width at half-maximum (FWHM) of 14.0 nm was observed from Eu(DBM)3(BrDPPz) in these double-layered PLEDs at dopant concentrations from 1 wt% to 8 wt%. For the PLED containing 1 wt% Eu(DBM)3(BrDPPz), a maximum luminance of 829 cd/m2 at 153.5 mA/cm2, highest external quantum efficiency of 1.70% at 2.1 mA/cm2 and maximum luminance of 0.74 cd/A at 4.31 mA/cm2 were obtained.

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Design and development of dithienopyrrolobenzothiadiazole (DTPBT)-based rigid conjugated polymers with improved hole mobilities

Donor-acceptor integrated ladder-type dithienopyrrolobenzothiadiazole (DTPBT)-based conjugated building blocks have been used to develop rigid conjugated polymers by copolymerizing them with synthesized ladder-type indoloquinoxaline, π-extended isoindigo and π-extended 2,1,3-benzothiadiazole-based conjugated building blocks. Structural aspects of synthesized building blocks are studied by single-crystal X-ray diffraction, which revealed the co-planar structure of indoloquinoxaline-scaffold while twisted but intramolecularly hydrogen-bonded structures of π-extended isoindigo- and 2,1,3-benzothiadiazole-scaffolds with number of intermolecular non-bonding interactions. The synthesized DTPBT-based conjugated polymers P-1, P-2 and P-3 are studied for photophysical and electrochemical properties and are found to have moderate to good visible light absorptivity with HOMO energy levels below ?5.0 eV. The X-ray diffraction studies indicate strong π?π stacking interactions induced face-on arrangement of polymer chains respective to the substrate. Polymers show π?π stacks promoted high space-charge limited current (SCLC) hole mobilities ranging between 5.6 × 10?4 –1.3 × 10?3 cm2V?1s?1. The obtained SCLC hole mobility data in tandem with the studied structural aspects of monomers and morphological aspects of polymers, suggest that the combination of ladder-type DTPBT-scaffolds (capable of intermolecular π?π interactions) with non-ladder-type planar and structurally rigid π-extended conjugated scaffolds (capable of intermolecular π?π and other non-bonding interactions) is beneficial for getting good hole mobilities.

A Novel Conjugated Polymer Consists of Benzimidazole and Benzothiadiazole: Synthesis, Photophysics Properties, and Sensing Properties for Pd2+

A conjugated polymer PPBIBTE based on benzimidazole and benzothiadiazole was synthesized through palladium-catalyzed sonogashira cross-coupling reaction. The chemical structures of the monomers and the polymer were indicated by 1H NMR, and investigation of photophysics properties and sensing optical properties for metal ions were observed by ultraviolet–visible and photoluminescence spectroscopy. PPBIBTE showed remarkable selectivity for Pd2+ by “turn-off” fluorescence sensing progress. In addition, the Stern–Volmer and Benesi-Hildebrand plots were used to reveal the interaction between the polymer and Pd2+, while job's method was applied to calculate the determination of stoichiometry. The results demonstrate that PPBIBTE can utilize static quenching for Pd2+ by forming a 1:1 complex. And it is a potential sensing material as fluorescence chemosensor for Pd2+ with high selectivity and sensitivity.

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Novel cathepsin K inhibitors block osteoclasts in vitro and increase spinal bone density in zebrafish

Cathepsin K (Cat K) is a predominant cysteine protease and highly potent collagenase expressed in osteoclasts. Cat K inhibitors are anti-resorptive agents to treat osteoporosis. A novel scaffold of cathepsin K inhibitors, exemplified by lead compound 1x, was used as the template for designing and synthesizing a total of 61 derivatives that have not been reported before. An exploratory structure-activity relationship analysis identified the potent Cat K inhibitor A22, which displayed an IC50 value of 0.44 μM against Cat K. A22 was very specific for Cat K and caused a significantly higher in vitro inhibition of the enzyme as compared to that of lead compound 1x. A surface plasmon resonance analysis confirmed in vitro binding of A22 to Cat K. Molecular docking studies indicated several favourable interaction sites for A22 within the active pocket of Cat K. Furthermore, A22 also blocked active osteoclasts in vitro and increased spinal bone density in zebrafish, in which it showed an activity that was higher than that of the marketed therapeutic bone metabolizer etidronate disodium. A22 represents a very promising lead compound for the development of novel antiresorptive agents functioning as orthosteric inhibitors of Cat K.

Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization

PRMT5 plays important roles in diverse cellular processes and is upregulated in several human malignancies. Besides, PRMT5 has been validated as an anticancer target in mantle cell lymphoma. In this study, we found a potent and selective PRMT5 inhibitor by performing structure-based virtual screening and hit optimization. The identified compound 17 (IC50 = 0.33 μM) exhibited a broad selectivity against a panel of other methyltransferases. The direct binding of 17 to PRMT5 was validated by surface plasmon resonance experiments, with a Kd of 0.987 μM. Kinetic experiments indicated that 17 was a SAM competitive inhibitor other than the substrate. In addition, 17 showed selective antiproliferative effects against MV4-11 cells, and further studies indicated that the mechanism of cellular antitumor activity was due to the inhibition of PRMT5 mediated SmD3 methylation. 17 may represent a promising lead compound to understand more about PRMT5 and potentially assist the development of treatments for leukemia indications.