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

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

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 
• 77-78-1 dimethyl sulfate 
• 63435-16-5 3-hydroxy-4-aminobenzoic acid methyl ester 
• 99-06-9 3-Carboxyphenol 

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 
• 776315-11-8 methyl 4-bromo-3-{[2-(4-morpholinyl)-2-oxoethyl]oxy}benzoate 
• 887757-26-8 methyl 4-bromo-3-(2-bromoethoxy)benzoate 
• 1352620-92-8 (4-bromo-3-methoxyphenyl)(morpholin-4-yl)methanone 
• 1623120-28-4 N-(2-chlorobenzyl)-3-(2-(dimethylamino)ethoxy)-4-(1H-pyrazol-4-yl)benzamide 
• 1623120-32-0 3-(2-(dimethylamino)ethoxy)-4-(1H-pyrazol-4-yl)benzoic acid 
• 1623120-31-9 methyl 3-(2-(dimethylamino)ethoxy)-4-(1H-pyrazol-4-yl)benzoate 
• 1623120-29-5 methyl 4-bromo-3-(2-(dimethylamino)ethoxy)benzoate 
• 1443764-04-2 tert-butyl [4-(2-{[4-(dimethylcarbamoyl)-2-methoxyphenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]carbamate 

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.

Mechanosensitive fluorescent probes, changing color like lobsters during cooking: Cascade switching variations

Fluorescent flipper probes have been introduced recently to image physical forces in biology. Their design is inspired by the combination of planarization and polarization that makes the color of astaxanthin, a carotenoid, turn blue in living lobsters or shrimps. Flipper probes are constructed around twisted dithienothiophene dimers. Upon planarization, donors and acceptors placed on both sides are coupled to generate push-pull systems that shift excitation maxima to the red, while the emission wavelength is mechanoinsensitive. To assure chemical stability, these donors and acceptors have to turn on only upon planarization. In living lobster, this is achieved most beautifully with non-covalent hydrogen bonds to and from the surrounding, planarizing protein. With flipper probes, the unorthodox chalcogen bonds prove best to produce turn-on donors and acceptors. The specific objective of this study was to explore different turn-on donors for the resulting chalcogen-bonding cascade switches. The focus is on substitution of the original triazoles with ethylenedioxythiophene (EDOT) and ortho-hydroxyphenyl (HOP) donors. Design, synthesis and evaluation of the respective flipper probes are described.

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.

Rhodium-Catalyzed Twofold Unsymmetrical C-H Alkenylation-Annulation/Thiolation Reaction to Access Thiobenzofurans

A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed, enabling the straightforward and efficient synthesis of various thiobenzofurans in one step. This robust protocol proceeds with a broad substrate scope and good functional group tolerance under relatively mild reaction conditions.

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.]

The Suzuki–Miyaura Cross-Coupling as the Key Step in the Synthesis of 2-Aminobiphenyls and 2,2'-Diaminobiphenyls: Application in the Synthesis of Schiff Base Complexes of Zn

2-Nitrophenylboronic acids serve as interesting starting materials for the construction of biphenyl- and terphenyl-based amines if subjected to the Suzuki–Miyaura reaction. Unfortunately, these boronic acids suffer from low reactivity in Suzuki reactions, alongside their low stability in the presence of Pd. Herein, a general method for the construction of 2-nitro-substituted bi- and terphenyls is presented, with special emphasis on the synthesis of 2-amino-2'-nitrobi- and terphenyls. Comparisons are made with other boronic acids that have some of the aforementioned issues. Finally, the application of the obtained 2-amino-2'-nitrobi- and terphenyls as starting materials for the synthesis of bi- and terphenyl based di- and triamines is encountered for, with emphasis on the use of these amines as precursors for Schiff base ligands. In addition, the synthesis of some Zn complexes of these ligands is presented.

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.

NOVEL COMPOUND AND PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF

A compound represented by the general formula (1) below or a pharmacologically acceptable salt thereof: [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.]

Structure-Based Approach to Identify 5-[4-Hydroxyphenyl]pyrrole-2-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

In an effort to find new and safer treatments for osteoporosis and frailty, we describe a novel series of selective androgen receptor modulators (SARMs). Using a structure-based approach, we identified compound 7, a potent AR (ARE EC50 = 0.34 nM) and selective (N/C interaction EC50 = 1206 nM) modulator. In vivo data, an AR LBD X-ray structure of 7, and further insights from modeling studies of ligand receptor interactions are also presented.

A facile color-tuning strategy for constructing a library of Ir(III) complexes with fine-tuned phosphorescence from bluish green to red using a synergetic substituent effect of -OCH3 and -CN at only the C-ring of C∧N ligand

By simply grafting a -CN group and/or a -OCH3 group onto the meta- and/or para-site of the C-ring, a series of Ir(iii) complexes bearing a similar molecular platform of bis(1,2-diphenyl-1H-benzimidazolato-N,C2′)iridium(iii)(acetylacetonate), but showing fine-tuned phosphorescence covering nearly the whole window of the visible spectrum with a wide color-tuning range of 109 nm was acquired. With the help of DFT calculations, it was revealed that if the C-related arene moiety of the C∧N ligand (C-ring) contributes substantially to both the HOMO and LUMO of an Ir(iii) complex, the concurrent introduction of an electron-donating -OCH3 and an electron-withdrawing -CN groups on the C-ring at the meta- and para-sites relative to the Ir atom may lead to a favorable synergetic substituent effect on the color-tuning direction. This may represent a facile yet effective molecular design strategy for Ir(iii) complexes with a desirous emission color. A bluish green organic light-emitting diode (OLED) based on one of the objective complexes displayed a maximum current efficiency of 62.1 cd A-1, an external quantum efficiency of 19.8%, and a brightness of 48-040 cd m-2, implying that high-performance red and blue OLED phosphors as well as libraries of Ir(iii) complexes bearing similar molecular platforms may be developed through this -OCH3 and -CN synergetic substitution strategy.