882772-99-8

Usage

Uses

Used in Pharmaceutical Industry:
3-bromo-2-nitrobenzaldehyde is used as an intermediate in the synthesis of peptidomimetic BACE1 inhibitors for the treatment of Alzheimer's disease. BACE1 (Beta-secretase 1) is an enzyme involved in the production of amyloid-beta peptides, which are implicated in the pathogenesis of Alzheimer's disease. By inhibiting BACE1, peptidomimetic inhibitors can potentially reduce the formation of amyloid-beta peptides and slow down the progression of the disease.

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 105205-49-0 C₁₀H₁₁BrN₂O₂ 
• 1261475-45-9 3-bromo-2-nitrobenzylic alcohol 
• 400629-31-4 2-(3-bromo-2-nitrophenyl)acetic acid 
• 13402-32-9 1,3-dibromo-2-nitrobenzene 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 145123-24-6 2-Amino-3-bromobenzaldehyde 
• 1169857-93-5 (S)-N-[(1E)-(3-bromo-2-nitrophenyl)methylene]-2-methylpropane-2-sulfinamide 
• 1261475-45-9 3-bromo-2-nitrobenzylic alcohol 
• 1006055-69-1 (E)-2-(3-bromo-2-nitrophenyl)-1-phenylsulfonylethene 

Relevant academic research and scientific papers

A 3 - bromo -2 - nitrobenzaldehyde chemical synthesis method

The invention relates to a chemical synthesis method of 3-bromo-2-nitrobenzaldehyde. The chemical synthesis method is characterized by using 1,3-dibromo-2-nitrobenzene as a raw material and carrying out five-step reactions including substitution, decarboxylation, oxidation, reduction and hydroformylation, and comprises the following steps of adding 1,3-dibromo-2-nitrobenzene, dimethyl malonate and alkali to an organic solvent to react to prepare 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate; dissolving 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate obtained in the former step in a tetrahydrofuran or acetone solvent, and adding a hydrochloric acid solution to react to prepare 2-(3-bromo-2-nitrobenzaldehyde)-acetic acid; adding a sodium hydroxide water solution and potassium permanganate to react to obtain 3-bromo-2-nitrobenzoic acid; dissolving 3-bromo-2-nitrobenzoic acid in the tetrahydrofuran solvent, and adding borane tetrahydrofuran to react to obtain 3-bromo-2-nitrobenzyl alcohol; adding 3-bromo-2-nitrobenzyl alcohol to a dichloromethane or 1,2-dichloroethane solvent and adding manganese dioxide to react to prepare 3-bromo-2-nitrobenzaldehyde. The synthetic route has the advantages of low cost and high yield.

Iron promoted C3-H nitration of 2H-indazole: direct access to 3-nitro-2H-indazoles

An efficient C3-H functionalization of indazole has been demonstrated. Notably, this method involves chelation-free radical C-H nitration on 2H-indazole. The radical mechanism was confirmed by control experiments and quantum chemical calculations. The synthetic utility has been proven by the synthesis of bio-relevant benzimidazoindazoles via reductive cyclization.

Reexamination of the bromination of 2-nitrobenzaldehyde with NBS or NaBr-NaIO4 in sulfuric acid

Two literature procedures for selective bromination of 2-nitrobenzaldehyde using N-bromosuccinimide (NBS) or NaBr-NaIO4 in sulfuric acid were examined. In contrast to the reports that 4-bromo-2-nitrobenzaldehyde is formed as a single product in good yield, reactions using NBS gave a number of isomeric mono- and dibrominated products identified by spectroscopical methods and by sodium borohydride reduction to the corresponding benzyl alcohol, and reactions using NaBr-NaIO4 did not furnish any product. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

A stereoselective approach to peptidomimetic BACE1 inhibitors

Aiming at identifying new scaffolds to generate beta-secretase (BACE1) inhibitors we developed peptidomimetics based on a 1,4-benzodiazepine core (3a-d), their seco-analogs (4a-b), and linear analogs (5a-h), by stereoselective approaches. We herein discuss the synthesis, molecular modeling and in vitro studies for the newly developed ligands. Compounds 5c and 5h behaved as BACE1 inhibitors on the isolated enzyme and in cellular studies. Particularly, for its low molecular weight, inhibitor 5h is a prototypic hit to develop a series of BACE1 inhibitors more potent and active on whole-cells.

Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators

The design and the synthesis of several chemical subclasses of imidazole containing γ-secretase modulators (GSMs) is described. Conformational restriction of pyridone 4 into bicyclic pyridone isosteres has led to compounds with high in vitro and in vivo p

NOVEL SUBSTITUTED INDAZOLE AND AZA-INDAZOLE DERIVATIVES AS GAMMA SECRETASE MODULATORS

The present invention is concerned with novel substituted indazole and aza-indazole derivatives of Formula (I), wherein R1, R2, R3, R4, Y, A1, A2, A3, A4, X1, X2, X3 and Het1 have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

New octahydropyrido[3,4-b]acridine scaffolds for combinatorial chemistry

Friedlaender reaction of aminobromobenzaldehydes with an optically active decahydroisoquinolone building block gave new octahydropyrido[3,4-b] acridines with quantitative regioselectivity. The products define a platform for combinatorial chemistry. Bromine functions could be reacted further using Suzuki, Heck, Sonogashira, and Buchwald-Hartwig reactions as well as cyanations. The secondary amino function was deprotected and coupled with amino acids and benzoic acid derivatives. A small model library has been prepared. Georg Thieme Verlag Stuttgart.