72517-15-8

Basic information

• Product Name: 5-BROMO-2,3-DIHYDROXY-BENZOIC ACID
• Synonyms: 5-BROMO-2,3-DIHYDROXY-BENZOIC ACID
• CAS NO: 72517-15-8
• Molecular Formula: C₇H₅BrO₄
• Molecular Weight: 233.0162
• Product Categories: Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 72517-15-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 5-BROMO-2,3-DIHYDROXY-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2,3-DIHYDROXY-BENZOIC ACID(72517-15-8)
• EPA Substance Registry System: 5-BROMO-2,3-DIHYDROXY-BENZOIC ACID(72517-15-8)

Safety Data

• Hazardous Substances Data: 72517-15-8(Hazardous Substances Data)

Usage

Description

5-BROMO-2,3-DIHYDROXY-BENZOIC ACID is an organic compound characterized by its pale yellow solid appearance. It is a derivative of benzoic acid with a bromine atom at the 5th position and two hydroxyl groups at the 2nd and 3rd positions. This chemical structure endows it with specific properties that make it suitable for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
5-BROMO-2,3-DIHYDROXY-BENZOIC ACID is used as a key intermediate compound for the synthesis of hydroxyalbuterol, a medication with bronchodilator properties. It helps in the treatment of respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD) by relaxing the muscles in the airways and improving breathing.
Used in Chemical Research:
5-BROMO-2,3-DIHYDROXY-BENZOIC ACID is also utilized in the preparation of bromo-dimethoxyphenyl oxadiazoles, which possess anti-Parkinson’s properties. These compounds are being investigated for their potential to alleviate the symptoms of Parkinson's disease, a neurodegenerative disorder that affects movement and coordination.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 721, 1960 DOI: 10.1021/jo01075a011

Upstream product

• 303-38-8 2,3-Dihydroxybenzoic acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 35090-76-7 5-bromo-2-hydroxy-3-methoxy-benzoic acid 

Downstream Products

• 105603-49-4 methyl 5-bromo-2,3-dihydroxybenzoate 
• 302945-05-7 5-bromo-2,3-bis-methoxycarbonyloxy-benzoic acid 
• 72517-23-8 5-bromo-2,3-dimethoxybenzoic acid 
• 83131-08-2 methyl 5-bromo-2,3-dimethoxybenzoate 
• 164670-73-9 2,3-dimethoxy-5-bromobenzobitrile 
• 107188-91-0 5-bromo-2,3-dimethoxybenzoic acid chloride 
• 1026468-85-8 5-Bromo-2,3-dimethoxy-benzamidine 
• 407610-18-8 2-(2,3-dimethoxy-5-bromophenyl)-4-(hydroxymethyl)imidazole 
• 1027904-03-5 2-(5-Bromo-2,3-dimethoxy-phenyl)-5-chloromethyl-1H-imidazole 
• 407610-17-7 N-tert-butyl-5-bromo-2,3-dimethoxybenzamide 
• 407610-20-2 2-(2,3-dimethoxy-5-bromophenyl)imidazole-4-carboxaldehyde 

Relevant articles and documents

POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M1

Described are positive allosteric modulators of muscarinic acetylcholine receptor M1 (mAChR M1), pharmaceutical compositions including the compounds, and methods of using the compounds and compositions for treating neurological disorders, psychiatric diso

Design, Synthesis, and Biological Evaluation of Quercetagetin Analogues as JNK1 Inhibitors

The recent discovery of c-Jun NH2-terminal kinase JNK1 suppression by natural quercetagetin (1) is a promising lead for the development of novel anticancer agents. Using both X-ray structure and docking analyses we predicted that 5′-hydroxy- (2

Molecular recognition at the active site of catechol-O-methyltransferase (COMT): Adenine replacements in bisubstrate inhibitors

L-Dopa, the standard therapeutic for Parkinson's disease, is inactivated by the enzyme catechol-O-methyltransferase (COMT). COMT catalyzes the transfer of an activated methyl group from S-adenosylmethionine (SAM) to its catechol substrates, such as L-dopa, in the presence of magnesium ions. The molecular recognition properties of the SAM-binding site of COMT have been investigated only sparsely. Here, we explore this site by structural alterations of the adenine moiety of bisubstrate inhibitors. The molecular recognition of adenine is of special interest due to the great abundance and importance of this nucleobase in biological systems. Novel bisubstrate inhibitors with adenine replacements were developed by structure-based design and synthesized using a nucleosidation protocol introduced by Vorbrueggen and co-workers. Key interactions of the adenine moiety with COMT were measured with a radiochemical assay. Several bisubstrate inhibitors, most notably the adenine replacements thiopyridine, purine, N-methyladenine, and 6-methylpurine, displayed nanomolar IC50 values (median inhibitory concentration) for COMT down to 6 nM. A series of six cocrystal structures of the bisubstrate inhibitors in ternary complexes with COMT and Mg2+ confirm our predicted binding mode of the adenine replacements. The cocrystal structure of an inhibitor bearing no nucleobase can be regarded as an intermediate along the reaction coordinate of bisubstrate inhibitor binding to COMT. Our studies show that solvation varies with the type of adenine replacement, whereas among the adenine derivatives, the nitrogen atom at position 1 is essential for high affinity, while the exocyclic amino group is most efficiently substituted by a methyl group. Copyright