3111-51-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Dibromo-5-hydroxybenzaldehyde is used as a key intermediate in the synthesis of LY-2801653, a c-Met receptor tyrosine kinase inhibitor. 2,4-Dibromo-5-hydroxybenzaldehyde plays a crucial role in the development of novel therapeutic agents targeting the c-Met receptor, which is implicated in various cancer types and other diseases.
Used in Chemical Synthesis:
In addition to its pharmaceutical applications, 2,4-Dibromo-5-hydroxybenzaldehyde is also utilized in various chemical synthesis processes. Its unique functional groups and structural properties make it a versatile building block for creating a wide range of organic compounds, including dyes, polymers, and other specialty chemicals.

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 67-66-3 chloroform 
• 7726-95-6 bromine 

Downstream Products

• 2737-21-5 2,4-dibromo-5-hydroxy-benzyl alcohol 
• 14348-39-1 2,4-dibromo-5-hydroxybenzoic acid 
• 4526-56-1 2,4-dibromo-6-chlorophenol 
• 174913-39-4 2,4-dibromo-6-chloro-anisole 
• 860725-06-0 4,6-dibromo-2-chloro-3-methoxy-benzaldehyde 
• 1580465-77-5 N¹-(2,4-dibromo-5-methoxybenzyl)-N³,N³-dimethylpropane-1,3-diamine 
• 1580465-76-4 2,4-dibromo-5-(((3-(dimethylamino)propyl)amino)methyl)phenol 
• 1206800-43-2 5-(2-Fluoro-4-nitrophenoxy)-1-methyl-6-(1 H-pyrazol-4-yl)-1H-indazole 
• 1577180-07-4 N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide 

Relevant academic research and scientific papers

2,4-Dibromo-5-hydroxybenzaldehyde

The title compound, C7H4Br2O2, crystallizes as centrosymmetric dimers in which two molecules are linked by two hydrogen bonds between the hydroxyl and carbonyl groups, with an O···O distance of 2.839 (5) angstro

TRK INHIBITOR AS ANTI-CANCER DRUG

The present disclosure relates to a group of tropomyosin receptor kinase inhibitors comprising an amido-phenoxy-indazole structure fragment. These compounds show potent inhibitory effects on various oncogenic kinases, especially TRK, and thus can be used

Preparation of tetrazole-fused π-conjugated molecules and their fluorescence behavior

New tetrazole-fused π-conjugated molecules were prepared from dibromobenzonitriles by repeated regioselective Sonogashira-Hagihara cross-coupling with acetylenes and intramolecular nucleophilic cyclizations. The conjugated tetracyclic compounds exhibited fluorescence with lifetimes of nanosecond order. From TD-DFT calculations, excited state wavefunctions of compounds indicated that the HOMO-1→LUMO and HOMO→LUMO+1 mainly became the first excited state (S0→S1) to contribute significantly to light emission.

Synthesis of cis-enamide macrocycles via ring-closing metathesis

Herein we report the synthesis of 13-, 14- and 15-membered cyclic lactams, using Grubbs' RCM method in 25, 52 and 46% yields respectively. The cis-enamide functional group was successfully introduced into these cyclic lactams by syn sulfoxide elimination

N1,N1-dimethyl-N3-(3-(trifluoromethyl) phenethyl)propane-1,3-diamine, a new lead for the treatment of human African trypanosomiasis

The natural product, convolutamine I (1), has anti-trypanosomal activity however it has a high molecular weight of 473 due to a presence of 3 bromine atoms. The synthesis of the natural product convolutamine I (1) together with its analogues are presented. A SAR study against Trypanosoma brucei brucei led to compounds with improved physico-chemical properties: lower molecular weight and lower log P while maintaining potency (with a slight 2-fold improvement).

Route design and development of a MET kinase inhibitor: A copper-catalyzed preparation of an N 1 - Methylindazole

The synthesis of a MET kinase inhibitor in an overall yield of 22% was achieved over eight steps starting with 3-hydroxybenzaldehyde, an improvement from the initial 12-step process with a 5.4% yield. Highlights of the process chemistry design and development are a Cu-catalyzed cyclization to form an important N1-methylindazole ring, a selective nitro reduction in the presence of an aryl bromide, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection to form the desired drug candidate.

Facile p-toluenesulfonic acid-promoted para-selective monobromination and chlorination of phenol and analogues

para-Regioselective bromination of phenol and analogues, promoted by p-toluenesulfonic acid, is achieved in high to excellent yields at room temperature with N-bromosuccinimide. Chlorination with N-chlorosuccinimide and catalysed by p-toluenesulfonic acid also gives para-chlorinated phenol analogues in good yields at room temperature. para-Bromination of phenol, promoted by p-toluenesulfonic acid, is achieved in excellent yields at room temperature with N-bromosuccinimide. p-Toluenesulfonic acid is also effective as a promoter of para-chlorination with N-chlorosuccinimide.

Asymmetric synthesis of amathamides A and B: Novel alkaloids isolated from Amathia wilsoni

Syntheses of the amathamides A and B ((2S)-N-[(E and Z)-2(2,4-dibromo-5-methoxyphenylethenyl]-1-methyl-2-pyrrolinecarboxamides), new alkaloids isolated from the Tasmanian marine bryozoan Amathia wilsoni, were accomplished by a sequence of reactions starting from 3-hydroxybenzaldehyde.