127972-00-3

Basic information

• Product Name: 2-Methoxy-5-methylphenylboronic acid
• Synonyms: 5-Methyl-2-methoxyphenylboronic acid;(2-methoxy-5-methylphenyl)boronic acid(SALTDATA: FREE);2-Methoxy-5-Methylphenylboronic Acid (contains varying aMounts of Anhydride);2-Methoxy-5-methylphenylboronic acid >=95%;CHEMBRDG-BB 4008663;AKOS BRN-0586;5-METHOXY-2-METHYLPHENYL BORONIC ACID;2-METHOXY-5-METHYLPHENYLBORONIC ACID
• CAS NO: 127972-00-3
• Molecular Formula: C₈H₁₁BO₃
• Molecular Weight: 165.98
• Product Categories: Aryl;Organoborons;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids;blocks;BoronicAcids;Substituted Boronic Acids;Heterocyclic Compounds;Alkoxy
• Mol File: 127972-00-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 92-97 °C(lit.)
• Boiling Point: 342.026 °C at 760 mmHg
• Flash Point: 160.652 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 2.97E-05mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in methanol.
• PKA: 8.65±0.58(Predicted)
• CAS DataBase Reference: 2-Methoxy-5-methylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-methylphenylboronic acid(127972-00-3)
• EPA Substance Registry System: 2-Methoxy-5-methylphenylboronic acid(127972-00-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-60-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 127972-00-3(Hazardous Substances Data)

Usage

Description

2-Methoxy-5-methylphenylboronic acid is an organic compound that belongs to the class of arylboronic acids. It is a white solid with the molecular formula C7H9BO3 and is characterized by the presence of a boron atom bonded to a phenyl ring with a methoxy and a methyl group as substituents. 2-Methoxy-5-methylphenylboronic acid is known for its versatile reactivity and stability, making it a valuable building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
2-Methoxy-5-methylphenylboronic acid is used as a reactant for the preparation of selective quinazolinyl-phenol inhibitors of CHK1, which have potential applications as antitumor and radioprotectant agents. These inhibitors play a crucial role in the regulation of cell cycle checkpoints and can be employed in the development of targeted cancer therapies.
Used in Chemical Synthesis:
2-Methoxy-5-methylphenylboronic acid is utilized as a reactant in various coupling reactions, such as the Rh-catalyzed asymmetric arylation of aldehydes and stereoselective hydroarylation reactions. These reactions are essential for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Suzuki-Miyaura Cross-Coupling:
2-Methoxy-5-methylphenylboronic acid is also used as a reactant in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for the formation of carbon-carbon bonds in organic synthesis. The reaction involves the coupling of an aryl or vinyl halide with an organoboron compound, such as 2-methoxy-5-methylphenylboronic acid, to form a new carbon-carbon bond. This reaction is particularly useful in the synthesis of biologically active molecules and materials with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H11BO3/c1-6-3-4-8(12-2)7(5-6)9(10)11/h3-5,10-11H,1-2H3

Upstream product

• 104-93-8 p-methylanizole 
• 121-43-7 Trimethyl borate 
• 22002-45-5 2-bromo-4-methylanisole 

Downstream Products

• 1152781-50-4 (E)-3-(2-methoxy-5-methylphenyl)-3-phenylacrylonitrile 
• 4373-61-9 2-(m-tolyl)pyridine 
• 865350-37-4 2-(2-methoxy-5-methylphenyl)pyridine 

Relevant articles and documents

Evidence for Oxidative Decay of a Ru-Bound Ligand during Catalyzed Water Oxidation

In the evaluation of systems designed for catalytic water oxidation, ceric ammonium nitrate (CAN) is often used as a sacrificial electron acceptor. One of the sources of failure for such systems is oxidative decay of the catalyst in the presence of the st

New 5-aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting

We designed and synthesized 48 aryl-1H-imidazole derivatives and investigated their in vitro growth inhibitory activity in cancer cell lines known to present various levels of resistance to proapoptotic stimuli. The IC50 in vitro growth inhibitory concentration of these compounds ranged from >100 μM to single digit μM. Among the most active compounds, 2i displayed similar in vitro growth inhibition in cancer cells independent of the cells' levels of resistance to proapoptotic stimuli and was found to be cytostatic in melanoma cell lines. Compound 2i was then tested by the National Cancer Institute Human Tumor Cell Line Anti-Cancer Drug Screen, and the NCI COMPARE algorithm did not reveal any correlation between its growth inhibition profiles with the NCI database compound profiles. The use of transcriptomically characterized melanoma models then enabled us to highlight mitochondrial targeting by 2i. This hypothesis was further confirmed by reactive oxygen production measurement and oxygen consumption analysis.

NOVEL COMPOUNDS

The invention relates to substituted phenoxyacetic acids (I) as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.