57543-36-9

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-2-HYDROXY-4-METHOXY-BENZALDEHYDE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to participate in different chemical reactions, contributing to the development of new drugs and medicinal compounds.
Used in Organic Chemistry Research:
In the field of organic chemistry, 5-BROMO-2-HYDROXY-4-METHOXY-BENZALDEHYDE is used as a reagent for its reactivity in forming heterocycles and other complex organic molecules, aiding in the advancement of chemical knowledge and the creation of novel chemical entities.

Upstream product

• 626-35-7 nitroacetic acid ethyl ester 
• 43192-31-0 2-bromo-4-methoxybenzaldehyde 
• 50-00-0 formaldehyd 
• 102127-34-4 4-bromo-3-methoxyphenol 
• 34841-06-0 3-bromo-4-methoxybenzylaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 6626-15-9 4-Bromoresorcinol 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 130333-46-9 5-bromo-2, 4-dimethoxybenzaldehyde 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 116096-90-3 5-bromo-2,4-dihydroxy-benzaldehyde 
• 77-78-1 dimethyl sulfate 
• 6615-24-3 2-hydroxy-4-methoxy-5-nitrobenzaldehyde 

Downstream Products

• 329217-84-7 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxy-6-hydroxybenzaldehyde 
• 20073-14-7 ethyl 2-(4-bromo-2-formyl-5-methoxyphenoxy)acetate 
• 84223-75-6 5-(2-Imidazolin-2-yl)-2-<4-(2-imidazolin-2-yl)phenyl>-6-methoxy-1-benzofuran-dihydrochlorid 
• 84223-76-7 2-(4-Amidinophenyl)-6-methoxy-1-benzofuran-5-carbonitril-hydrochlorid 
• 84223-74-5 2-(4-Cyanphenyl)-6-methoxy-1-benzofuran-5-carbonitril 
• 84223-71-2 5-Brom-2-(4-cyanphenyl)-6-methoxy-1-benzofuran 
• 552846-01-2 4-methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thien-2-yl-benzaldehyde 

Relevant academic research and scientific papers

Discovery of 2H-Chromen-2-one Derivatives as G Protein-Coupled Receptor-35 Agonists

A family of 2H-chromen-2-one derivatives were identified as G protein-coupled receptor-35 (GPR35) agonists using dynamic mass redistribution assays in HT-29 cells. The compounds with 1H-tetrazol-5-yl in 3-substituted position displayed higher potency than the corresponding carboxyl analogs, and the hydroxyl group in the 7-position also played an important role in GPR35 agonistic activity. 6-Bromo-7-hydroxy-8-nitro-3-(1H-tetrazol-5-yl)-2H-chromen-2-one (50) was found to be the most potent GPR35 agonist with an EC50 of 5.8 nM. Calculating the physicochemical properties of compounds with moderate to high potency suggested that compounds 30, 50, and 51 showed good druggability. This study provides a novel series of GPR35 agonists, and compound 50 may be a powerful tool to study GPR35.

1,4-DISUBSTITUTED PYRIDAZINE DERIVATIVES AND THEIR USE FOR TREATING SMN-DEFICIENCY-RELATED CONDITIONS

The present invention provides a compound of formula IA or a pharmaceutically acceptable salt thereof; 5 (IA) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

Synthesis of C4-C5 cycloalkyl-fused and C6-modified chromans via ortho-quinone methides

Starting from 3,5-dimethoxybenzaldehyde, some functionalized 2,3,4-trisubstituted tricyclic 4,5-cycloalkyl-fused and 6-modified chromans could be prepared via ortho-quinone methides (o-QMs)/hetero-Diels-Alder (HDA) reactions of the appropriate precursors.

Aldehyde-Assisted Ruthenium(II)-Catalyzed C-H Oxygenations

Versatile ruthenium(II) complexes allow for site-selective C-H oxygenations with weakly-coordinating aldehydes. The challenging C-H functionalizations proceed with high chemoselectivity by rate-determining C-H metalation. The new method features an ample substrate scope, which sets the stage for the step-economical preparation of various bioactive heterocycles.

Synthesis of 8-aryl-substituted coumarins based on ring-closing metathesis and Suzuki-Miyaura coupling: Synthesis of a furyl coumarin natural product from Galipea panamensis

The synthesis of 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, a natural product with antileishmanial activity recently isolated from the plant Galipea panamensis, is described. The key step is a Suzuki-Miyaura coupling of a furan-3-boronic acid and an

Discovery of XL413, a potent and selective CDC7 inhibitor

CDC7 is a serine/threonine kinase that has been shown to be required for the initiation and maintenance of DNA replication. Up-regulation of CDC7 is detected in multiple tumor cell lines, with inhibition of CDC7 resulting in cell cycle arrest. In this paper, we disclose the discovery of a potent and selective CDC7 inhibitor, XL413 (14), which was advanced into Phase 1 clinical trials. Starting from advanced lead 3, described in a preceding communication, we optimized the CDC7 potency and selectivity to demonstrate in vitro CDC7 dependent cell cycle arrest and in vivo tumor growth inhibition in a Colo-205 xenograft model.

Aromatic bromination of aldehydes and ketones using 1,3-di-n- butylimidazolium

An environmentally benign and efficient process for the preparation of monobromo derivatives of aryl aldehydes and ketones was developed by simple and practical reactions of aryl aldehydes or ketones with 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3), as a brominating reagent under solvent-free conditions in very high yields. The process has several advantages: high conversions, short reaction time, mild reaction conditions, simple workup with good to quantitative yields and re-usable ionic liquid.

Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides

Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed.

Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes

(Chemical Equation Presented) 2-Arylchromans were readily prepared from the hetero-Diels-Alder reactions of styrenes with the ortho-quinone methides (o-QMs) which, in turn, were generated by treating the MOM-protected benzylacetate derivatives with p-TsOH immobilized on silica (PTS-Si) in toluene under mild conditions (0°C to rt). The corresponding chromans were obtained in moderate to excellent yields (42-97%) and in moderate to excellent diastereoselectivity (up to >99:1).

ortho-Formylation of oxygenated phenols

Oxygenated phenols are mono-formylated using a mixture of paraformaldehyde, MgCl2, and Et3N in THF. In all cases but one, only one regioisomer of the salicylaldehyde is obtained in good to high yield.