269410-23-3

Basic information

• Product Name: 3-HYDROXY-4-METHOXYPHENYLBORONIC ACID
• Synonyms: 3-HYDROXY-4-METHOXYPHENYLBORONIC ACID;3-Hydroxy-4-methoxyphenylboronic acid, pinacol ester;2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS NO: 269410-23-3
• Molecular Formula: C₁₃H₁₉BO₄
• Molecular Weight: 250.1
• Mol File: 269410-23-3.mol

Chemical Properties

• Boiling Point: 369.1°Cat760mmHg
• Flash Point: 177°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 5.74E-06mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: 2-8°C
• PKA: 10.02±0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXY-4-METHOXYPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-4-METHOXYPHENYLBORONIC ACID(269410-23-3)
• EPA Substance Registry System: 3-HYDROXY-4-METHOXYPHENYLBORONIC ACID(269410-23-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 269410-23-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Hydroxy-4-Methoxyphenylboronic acid is used as a building block in the organic synthesis industry for the development of various pharmaceuticals and agrochemicals. Its unique structure allows for the formation of carbon-carbon bonds, making it a valuable component in the creation of complex molecules.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
In the field of organic chemistry, 3-Hydroxy-4-Methoxyphenylboronic acid is utilized as a reagent in Suzuki-Miyaura cross-coupling reactions. This reaction is a powerful method for forming carbon-carbon bonds, which is crucial for the synthesis of a wide range of organic compounds, including those with potential biological activity.
Used in the Synthesis of Biologically Active Compounds:
3-Hydroxy-4-Methoxyphenylboronic acid is employed in the synthesis of biologically active compounds due to its ability to contribute to the formation of complex molecular structures. Its presence in these compounds can enhance their potential therapeutic effects, making it a valuable tool in the development of new drugs and agrochemicals.

InChI:InChI=1/C13H19BO4/c1-12(2)13(3,4)18-14(17-12)9-6-7-11(16-5)10(15)8-9/h6-8,15H,1-5H3

Upstream product

• 37942-01-1 5-bromo-2-methoxyphenol 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1312996-89-6 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)cyclopent-1-en-1-yl]phenol 
• 1449300-67-7 N-{4-[2-amino-5-(3-hydroxy-4-methoxyphenyl)pyridin-3-yl]phenyl}-5-(4-fluorophenyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydropyridine-3-carboxamide 
• 501-19-9 chavibetol 

Relevant articles and documents

Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties

Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clinical trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiological conditions, reducing the overall activity of the drug candidates. Herein, we report the preparation of cis-restrained carbocyclic analogs of CA-4. The compounds, which differ by the size and hybridization of the carbocyclic ring have been evaluated for their cytotoxic properties and their ability to inhibit tubulin polymerization. Biological data, supported by molecular docking studies, identified cyclobutenyl and cyclobutyl derivatives of the natural product as highly promising drug candidates.

EBNA1 INHIBITORS AND THEIR METHOD OF USE

Pharmaceutical compositions of the invention comprise EBNA1 inhibitors useful for the treatment of diseases caused by EBNA1 activity such as cancer, infectious mononucleosis, chronic fatigue syndrome, multiple sclerosis, systemic lupus erythematosus and rheumatoid arthritis. Pharmaceutical compositions of the invention also comprise EBNA1 inhibitors useful for the treatment of diseases caused by latent Epstein-Barr Virus (EBV) infection. Pharmaceutical compositions of the invention also comprise EBNA1 inhibitors useful for the treatment of diseases caused by lytic Epstein-Barr Virus (EBV) infection.

Hydroboronation process

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.