5274-71-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-nitrobenzaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromo-4-nitrobenzaldehyde serves as a crucial component in the production of pesticides and other crop protection agents, contributing to enhanced agricultural productivity.
Used in Dye and Perfume Industry:
2-Bromo-4-nitrobenzaldehyde is utilized as an intermediate in the synthesis of dyes and perfumes, enabling the creation of a diverse range of colorants and fragrances for various applications.
Safety Precautions:
It is important to handle 2-Bromo-4-nitrobenzaldehyde with care due to its toxic nature. Exposure to 2-Bromo-4-nitrobenzaldehyde can cause skin irritation and respiratory issues. Proper safety measures, including the use of personal protective equipment and adherence to handling protocols, should be implemented to minimize health risks.

InChI:InChI=1/C16H17BrN2O3S/c1-3-5-11-14(16(20)21-4-2)13(10(7-18)15(19)22-11)12-6-9(17)8-23-12/h6,8,13H,3-5,19H2,1-2H3

Upstream product

• 16426-64-5 2-bromo-4-nitrobenzoic acid 
• 940-05-6 2-bromo-1-(bromomethyl)-4-nitrobenzene 
• 7745-93-9 2-bromo-4-nitrotoluene 
• 470715-98-1 acetic acid acetoxy-(2-bromo-4-nitro-phenyl)-methyl ester 

Downstream Products

• 179129-21-6 4-Nitro-2-<(trimethylsilyl)ethynyl>benzaldehyde 
• 1246965-75-2 C₉H₄BrClF₃NO₂ 
• 1341231-16-0 2-(hex-1-ynyl)-4-nitrobenzaldehyde 
• 186390-79-4 6-Nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 267648-14-6 3-bromo-4-(oxazol-5-yl)aniline 
• 1393679-85-0 C₁₇H₁₅BrN₂O₃ 
• 1388624-57-4 (R,E)-2-bromo-5-nitrobenzaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime 
• 1313762-43-4 4-nitro-2-vinylbenzaldehyde 
• 22246-24-8 5-nitro-2,3-dihydroinden-1-one 

Relevant academic research and scientific papers

Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.

ARYL AMIDE KINASE INHIBITORS

The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor

The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clinical candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesising a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, commercially available precursor is discussed.

Versatile synthesis of isoquinolines and isochromenes by Pd-catalyzed oxidative carbonylation of (2-alkynyl)benzylideneamine derivatives

Isoquinoline-4-carboxylic esters 3 and isochromene-4-carboxylic esters 4 have been conveniently prepared by direct PdI2-catalyzed oxidative heterocyclization/alkoxycarbonylation of readily available (2- alkynylbenzylidene)amine derivatives. In particular, (2-alkynylbenzylidene) (tert-butyl)amines 2 selectively afforded isoquinoline derivatives 3 by N-cyclization, whereas N-(2-alkynylbenzylidene)-N′-phenylhydrazines 5 led to the formation of isochromenes 4 through O-cyclization ensuing from water attack on the imino group of the substrate. Reactions were carried out in alcoholic solvents at 80-100 °C and under 20-80 atm (at 25 °C) of a 4:1 mixture of CO/air, in the presence of PdI2 (2-10 mol-%) in conjunction with KI (KI/PdI2 molar ratio = 10). In the case of imines 2, the use of a dehydration agent, such as trialkyl orthoformate, was necessary to obtain satisfactory yields of isoquinolines 3.

Inter- and intramolecular hydroacylation of alkenes employing a bifunctional catalyst system

Based on a conceptually innovative bifunctional P,N ligand, an efficient protocol for the rhodium-catalyzed inter- and intramolecular hydroacylation of alkenes has been developed.

Inhibitors of inosine monophosphate dehydrogenase: SARs about the N-[3-methoxy-4-(5-oxazolyl)phenyl moiety

The first reported structure-activity relationships (SARs) about the N-[3-methoxy-4-(5-oxazolyl)phenyl moiety for a series of recently disclosed inosine monophosphate dehydrogenase (IMPDH) inhibitors are described. The syntheses and in vitro inhibitory values for IMPDH II, and T-cell proliferation (for select analogues) are given.

Novel diamide-based inhibitors of IMPDH

A series of novel amide-based small molecule inhibitors of inosine monophosphate dehydrogenase is described. The synthesis and the structure-activity relationships (SARs) derived from in vitro studies are presented.