106291-80-9

Basic information

• Product Name: METHYL 4-BROMO-3-HYDROXYBENZOATE
• Synonyms: 4-BROMO-3-HYDROXY-BENZOIC ACIDMETHYL ESTER;METHYL 4-BROMO-3-HYDROXYBENZOATE;Methyl 4-bromo-3-hydroxybenzoate 98%;2-Bromo-5-(methoxycarbonyl)phenol;Methyl 3-hydroxy-4-bromobenzoate;Methyl 4-Bromo-3-hydroxybenzoate, >=98%
• CAS NO: 106291-80-9
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• Product Categories: blocks;Bromides;Carboxes
• Mol File: 106291-80-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 121-125
• Boiling Point: 318 °C at 760 mmHg
• Flash Point: 146.1 °C
• Appearance: /
• Density: 1.627 g/cm³
• Vapor Pressure: 0.0002mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Keep Cold
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: 7.61±0.10(Predicted)
• CAS DataBase Reference: METHYL 4-BROMO-3-HYDROXYBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-BROMO-3-HYDROXYBENZOATE(106291-80-9)
• EPA Substance Registry System: METHYL 4-BROMO-3-HYDROXYBENZOATE(106291-80-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 106291-80-9(Hazardous Substances Data)

Usage

Description

METHYL 4-BROMO-3-HYDROXYBENZOATE is an organic compound characterized by its burgundy color. It is a derivative of benzoic acid with a bromine atom at the 4-position and a hydroxyl group at the 3-position, attached to a methyl ester. This chemical structure endows it with unique properties that make it suitable for various applications.

Uses

Used in Pharmaceutical Industry:
METHYL 4-BROMO-3-HYDROXYBENZOATE is used as a reactant for the preparation of selective inhibitors. Its unique chemical structure allows it to be a key component in the synthesis of compounds that can specifically target and inhibit certain biological processes or enzymes, which can be beneficial in the development of new drugs for various medical conditions.
Used in Chemical Synthesis:
METHYL 4-BROMO-3-HYDROXYBENZOATE can also be utilized as an intermediate in the synthesis of other organic compounds. Its bromine atom and hydroxyl group make it a versatile building block for creating a wide range of molecules with different properties and applications in various industries, such as materials science, agrochemicals, and dyes.
Used in Research and Development:
Due to its distinctive chemical properties, METHYL 4-BROMO-3-HYDROXYBENZOATE can be employed in research and development for studying the effects of structural modifications on the properties and reactivity of benzoic acid derivatives. This can lead to the discovery of new compounds with improved or novel functionalities, which can be applied in various fields, including pharmaceuticals, materials science, and environmental science.

InChI:InChI=1/C8H7BrO3/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4,10H,1H3

Upstream product

• 67-56-1 methanol 
• 14348-38-0 4-bromo-3-hydroxybenzoic acid 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 99-06-9 3-Carboxyphenol 
• 63435-16-5 3-hydroxy-4-aminobenzoic acid methyl ester 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 17100-63-9 methyl 4-bromo-3-methoxybenzoate 
• 438571-11-0 4-bromo-3-[2-(2,4-dichloro-phenyl)-ethoxy]-benzoic acid methyl ester 
• 870779-63-8 methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate 
• 870779-64-9 4-bromo-3-(tetrahydropyran-2-yloxy)benzyl alcohol 
• 870779-65-0 4-bromo-3-(tetrahydropyran-2-yloxy)benzyl bromide 
• 870779-66-1 4-{[4-bromo-3-(tetrahydropyran-2-yloxy)benzyl][1,2,4]triazol-4-ylamino}benzonitrile 
• 870779-67-2 4-[(4-bromo-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole 
• 438571-12-1 4-bromo-3-[2-(2,4-dichloro-phenyl)-ethoxy]-benzoic acid 
• 849333-67-1 4-bromo-3-phenoxybenzoic acid 
• 1027553-82-7 2-(4-bromo-3-phenoxy-phenyl)-5-methoxy-benzo[d][1,3]oxazin-4-one 
• 849333-69-3 2-(4-bromo-3-phenoxybenzoylamino)benzoic acid methyl ester 
• 849334-05-0 2-(4-bromo-3-phenoxybenzoylamino)-6-methoxybenzoic acid 

Relevant articles and documents

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

New triazine-based tricarboxylic acid linkers were prepared as elongated relatives of triazinetribenzoic acid (TATB). Additionally, functional groups (NO2, NH2, OMe, OH) were introduced for potential post-synthetic modification (PSM) of MOFs. Functionalized tris(4-bromoaryl)triazine "cores" (3a,3b) were obtained by unsymmetric trimerization mixing one equivalent of an acid chloride (OMe or NO2 substituted) with two equivalents of an unsubstituted nitrile. Triple Suzuki coupling of the cores 3 with suitable phenyl- and biphenylboronic acid derivatives provided elongated tricarboxylic acid linkers as carboxylic acids 17 and 20 or their esters 16 and 19. Reduction of the nitro group and cleavage of the methoxy group gave the respective amino and hydroxy-substituted triazine linkers.

Structure-Based Optimization of Small-Molecule Inhibitors for the β-Catenin/B-Cell Lymphoma 9 Protein-Protein Interaction

Structure-based optimization was conducted to improve the potency, selectivity, and cell-based activities of β-catenin/B-cell lymphoma 9 (BCL9) inhibitors based on the 4′-fluoro-N-phenyl-[1,1′-biphenyl]-3-carboxamide scaffold, which was designed to mimic the side chains of the hydrophobic α-helical hot spots at positions i, i + 3, and i + 7. Compound 29 was found to disrupt the β-catenin/BCL9 protein-protein interaction (PPI) with a Ki of 0.47 μM and >1900-fold selectivity for β-catenin/BCL9 over β-catenin/E-cadherin PPIs. The proposed binding mode of new inhibitors was consistent with the results of site-directed mutagenesis and structure-activity relationship studies. Cell-based studies indicated that 29 disrupted the β-catenin/BCL9 interaction without affecting the β-catenin/E-cadherin interaction, selectively suppressed transactivation of Wnt/β-catenin signaling, downregulated expression of Wnt target genes, and inhibited viability of Wnt/β-catenin-dependent cancer cells in dose-dependent manners. A comparison of the biochemical and cell-based assay results offered the directions for future inhibitor optimization.

THERAPEUTIC AGENT FOR INFLAMMATORY DISEASES, AUTOIMMUNE DISEASES, FIBROTIC DISEASES, AND CANCER DISEASES

A therapeutic agent for treating at least one disease selected from the group consisting of inflammatory diseases, autoimmune diseases, fibrotic diseases, and cancer diseases, comprising: at least one selected from the group consisting of a compound represented by the following general formula (1) and pharmacologically acceptable salts thereof as an active ingredient. [In the formula (1), R1 and R2 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a carboxy group, a cyano group, an optionally substituted C1-6 alkyl group et al.; R3 represents a hydrogen atom; R4 represents an optionally substituted 4- to 10-membered monocyclic heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom; X represents a group represented by the following formula: -CH2-, - CH2-CH2-, -CH2-CH2-CH2-, or -CH2-O-CH2-; and Z represents a hydrogen atom or a hydroxyl group.]

INHIBITORS FOR THE Β-CATENIN/B-CELL LYMPHOMA 9 (BCL9) PROTEIN–PROTEIN INTERACTION

Disclosed are inhibitors for the β-catenin/BCL9 interaction. The inhibitors are selective for β-catenin/BCL9 over β-catenin/cadherin interactions. Methods of using the disclosed compounds to treat cancer are also disclosed.