39232-03-6

Usage

Physical state

Pale yellow to brownish liquid

Classification

Halogenated aromatic amine

Common uses

Production of dyes, pharmaceuticals, and other organic compounds

Applications

Synthesis of various organic compounds, production of agricultural chemicals, pharmaceuticals, and dyes

Safety precautions

Handling and use should be done with appropriate safety measures in a well-ventilated environment

InChI:InChI=1/C8H10BrN/c9-6-5-7-1-3-8(10)4-2-7/h1-4H,5-6,10H2

Upstream product

• 5339-26-4 (4-nitrophenyl)ethyl bromide 
• 104-10-9 2-(4'-aminophenyl)ethyl alcohol 
• 149068-81-5 1-azido-4-(2-bromoethyl)benzene 
• 100-27-6 2-(4-nitrophenyl)ethanol 

Downstream Products

• 72054-56-9 4-(2-bromoethyl)benzonitrile 
• 1118752-46-7 C₁₇H₂₁N₇ 
• 1118752-47-8 C₁₉H₂₅N₇ 
• 1118752-48-9 C₁₉H₂₅N₇ 
• 1118752-49-0 C₁₇H₂₁N₇ 
• 39232-06-9 2-bromo-1-[4-(acetylamino)phenyl]-ethane 
• 115519-20-5 trans-4-(2-bromoethyl)-1-trifluoromethoxybenzene 
• 218943-57-8 1-(2-bromoethyl)(4-t-butoxycarbonylamino)benzene 
• 864529-66-8 N-[4-(2-azidoethyl)phenyl]acetamide 
• 1346427-62-0 C₁₃H₁₀Br₃N₇O₂ 
• 1346427-54-0 C₁₁H₇Br₃N₄ 
• 1346427-48-2 C₁₁H₉Br₃N₄O 

Relevant academic research and scientific papers

Silver nanoparticles supported on P, Se-codoped g-C3N4 nanosheet as a novel heterogeneous catalyst for reduction of nitroaromatics to their corresponding amines

P, Se-codoped g-C3N4 (PSeCN) nanosheet was in situ prepared by facile thermal polymerization of melamine, phosphonitrilic chloride trimer, and selenium black powder as the precursors. It was found as a suitable support for the immobilization of silver nanoparticles (Ag NPs). The prepared nanocatalyst was fully characterized via standard analysis methods including EDX, ICP-OES, XRD, FT-IR, SEM, TEM, and BET. This PSeCN/Ag nanocatalyst with a higher specific surface area compared with CN, showed excellent catalytic activity towards the reduction of several nitroaromatic compounds using sodium borohydride (NaBH4) in short reaction times with high efficiency and good selectivity in water as a green solvent. Significantly, the above-mentioned nanocomposite could be reused six times without appreciable loss of its catalytic activity.

Cobalt oxide NPs immobilized on environmentally benign biological macromolecule-derived N-doped mesoporous carbon as an efficient catalyst for hydrogenation of nitroarenes

Highly nitrogen-doped mesoporous carbon (N-mC) material incorporated cobalt oxide nanoparticles was synthesized through simple pyrolysis of environmentally friendly chitosan-polyaniline-Co(OAc)2 precursor in one-step. The as-prepared catalyst named CoO&at;N-mC with 14.65 ?wtpercent nitrogen content was characterized by different analysis techniques. The heterogeneous catalyst exhibits outstanding catalytic activity for the reduction of a variety of nitroaromatic compounds in the presence of NaBH4 as a reducing agent in water as a green solvent at 75 ?°C. Utilization of natural biological macromolecules such as chitosan as green and cheap starting material with harmless aniline and earth-abundant cobalt salt, facile synthesis, excellent product yield, short reaction time, high chemoselectivity, sustainable and mild reaction condition, and reusability of catalyst for at least five cycles without any significant decline in the catalytic efficiency are some prominent merits of this new nanocatalyst.

Rapid and convenient conversion of nitroarenes to anilines under microwave conditions using nonprecious metals in mildly acidic medium

Nitroarenes are reduced to the corresponding aniline derivatives using iron or zinc under mild conditions under microwave heating conditions. Mild acidity is provided by ammonium chloride in an aqueous methanol medium. The conditions are tolerant to other functional groups, with the exception of bromoalkyl derivatives, which yield complex reaction mixtures; otherwise, yields are generally quite high (80–99%).

Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer’s Agents Based on Rational Design

Glutaminyl cyclase (QC) has been implicated in the formation of toxic amyloid plaques by generating the N-terminal pyroglutamate of β-amyloid peptides (pGlu-Aβ) and thus may participate in the pathogenesis of Alzheimer’s disease (AD). We designed a library of glutamyl cyclase (QC) inhibitors based on the proposed binding mode of the preferred substrate, Aβ3E?42. An in vitro structure-activity relationship study identified several excellent QC inhibitors demonstrating 5- to 40-fold increases in potency compared to a known QC inhibitor. When tested in mouse models of AD, compound 212 significantly reduced the brain concentrations of pyroform Aβ and total Aβ and restored cognitive functions. This potent Aβ-lowering effect was achieved by incorporating an additional binding region into our previously established pharmacophoric model, resulting in strong interactions with the carboxylate group of Glu327 in the QC binding site. Our study offers useful insights in designing novel QC inhibitors as a potential treatment option for AD.

Synthesis and docking of novel piperidine renin inhibitors

A series of 4-triazolyl-substituted piperidine derivatives were synthesized from N-Boc protected trans-4-ethynyl-3-hydroxypiperidine and tested as novel renin inhibitors. Piperidine derivatives containing a 1-substituted 1,2,3-triazol-5-yl substituent were found to be most active. Molecular docking experiments provide a rank order that is in agreement with experimental data. Furthermore, all compounds explore the S1 and the S3 subpockets through the piperidine substituents.

Conversion of systemically-distributed triazole-based stearoyl-CoA desaturase (SCD) uHTS hits into liver-targeted SCD inhibitors

It has been demonstrated that once-a-day dosing of systemically-distributed SCD inhibitors leads to adverse events in eye and skin. Herein, we describe our efforts to convert a novel class of systemically-distributed potent triazole-based uHTS hits into liver-targeted SCD inhibitors as a means to circumvent chronic toxicity.

A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system

Using a system that accelerates the serendipitous discovery of new reactions by evaluating hundreds of DNA-encoded substrate combinations in a single experiment, we explored a broad range of reaction conditions for new bond-forming reactions. We discovered reactivity that led to a biomolecule-compatible, Ru(II)-catalysed azide-reduction reaction induced by visible light. In contrast to current azide-reduction methods, this reaction is highly chemoselective and is compatible with alcohols, phenols, acids, alkenes, alkynes, aldehydes, alkyl halides, alkyl mesylates and disulfides. The remarkable functional group compatibility and mild conditions of the reaction enabled the azide reduction of nucleic acid and oligosaccharide substrates, with no detectable occurrence of side reactions. The reaction was also performed in the presence of a protein enzyme without the loss of enzymatic activity, in contrast to two commonly used azide-reduction methods. The visible-light dependence of this reaction provides a means of photouncaging functional groups, such as amines and carboxylates, on biological macromolecules without using ultraviolet irradiation.

COMPOUND WITH SEROTONINERGIC ACTIVITY, PROCESS FOR PREPARING IT AND PHARMACEUTICAL COMPOSITION COMPRISING IT

Compound of formula (I) in which R1, R2 and R3 are defined in the following description, and the pharmaceutically acceptable acid-addition or base-addition salts thereof. The invention also relates to a process and an intermediate for preparing it, and to a pharmaceutical composition comprising it. The invention also relates to the use of a novel 2H-pyrrolo[3,4-c]quinoline compound for preparing a pharmaceutical composition that is active in the treatment of disturbances of the serotoninergic system.

Synthesis and evaluation of functionalized isoindigos as antiproliferative agents

A series of functionalized isoindigos structurally related to meisoindigo (1-methylisoindigo), a therapeutic agent used for the treatment of a form of leukemia, were synthesized and evaluated for antiproliferative activities on a panel of human cancer cells. Two promising compounds (1 -phenpropylisoindigo and 1-(p-methoxy-phenethyl)-isoindigo) that were more potent than meisoindigo and comparable to 6bromoindirubin-3'-oxime on leukemic K562 and liver HuH7 cells were identified. Structure-activity relationships showed the importance of keeping one of the lactam NH in an unsubstituted state. Substitution of the other lactam NH with aryl or arylalkyl side chains retained or improved activity in most instances. An intact exocyclic double bond was also essential, possibly to maintain planarity and rigidity of the isoindigo scaffold. None of the compounds were found to inhibit CDK2 in an in vitro assay, in spite of reports linking the antiproliferative activities of meisoindigo and other isoindigos to CDK2 inhibition. Hence, these functionalized isoindigos disrupted cell growth and proliferation by other mechanistic pathways that did not involve CDK2 inhibition.

One step hair coloring compositions using salts

A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.