190788-60-4

Basic information

• Product Name: 2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• Synonyms: 2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(2-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-METHOXYPHENYLBORONIC ACID, PINACOL ESTER;2-METHOXYBENZENEBORONIC ACID, PINACOL ESTER;2-Methoxybenzeneboronic acid, pinacol ester 97%;2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-;2-(2-Methoxyloxyphenyl)-4;2-Methoxy-1-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzene
• CAS NO: 190788-60-4
• Molecular Formula: C₁₃H₁₉BO₃
• Molecular Weight: 234.1
• Product Categories: blocks;BoronicAcids
• Mol File: 190788-60-4.mol
• Article Data: 71

Chemical Properties

• Melting Point: 78-80
• Boiling Point: 328.5 °C at 760 mmHg
• Flash Point: 152.5 °C
• Appearance: /
• Density: 1.02 g/cm³
• Vapor Pressure: 0.00036mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(190788-60-4)
• EPA Substance Registry System: 2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(190788-60-4)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 190788-60-4(Hazardous Substances Data)

Usage

Description

2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, also known as 2-Methoxyphenylboronic Acid Pinacol Ester, is an organic compound with the molecular formula C12H19BO3. It is a derivative of boronic acid and is characterized by its pinacol ester functional group. 2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is known for its potential applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-(2-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a key intermediate compound for the synthesis of inhibitors targeting TGF-β1 and activin A signaling pathways. These inhibitors play a crucial role in regulating cellular processes such as cell proliferation, differentiation, and migration, which are often dysregulated in various diseases, including cancer. By modulating these signaling pathways, the compound can potentially contribute to the development of novel therapeutic strategies for treating diseases associated with abnormal TGF-β1 and activin A signaling.

InChI:InChI=1/C13H19BO3/c1-12(2)13(3,4)17-14(16-12)10-8-6-7-9-11(10)15-5/h6-9H,1-5H3

Upstream product

• 17763-67-6 Phenyl triflate 
• 59099-58-0 2-methoxyphenyl triflate 
• 578-57-4 2-bromoanisole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 766-51-8 2-Chloroanisole 
• 73183-34-3 bis(pinacol)diborane 
• 100-66-3 methoxybenzene 
• 529-28-2 4-iodoanisol 
• 16419-60-6 2-Methylphenylboronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 90-04-0 2-methoxy-phenylamine 
• 22092-92-8 diisopropopylaminoborane 

Downstream Products

• 5720-06-9 2-Methoxyphenylboronic acid 
• 867182-19-2 pinacol (+/-)-1-acetamido-1-(2-methoxyphenyl)methane-boronate 
• 867182-09-0 pinacol (+/-)-1-benzamido-1-(2-methoxyphenyl)methane-boronate 
• 867181-99-5 (+/-)-1-acetamido-1-(2-methoxyphenyl)methaneboronic acid 
• 867182-01-2 (+/-)-1-benzamido-1-(2-methoxyphenyl)methaneboronic acid 
• 890079-91-1 9,9'-bis(3,7-dimethyloctyl)-2,2'-bis(3,7-dimethyloctyloxy)-6,6'-bis(2-methoxyphenyl)-[3,3']-bicarbazolyl 
• 4957-17-9 1-methoxy-2-(3-methylbut-2-en-1-yl)benzene 
• 1240389-99-4 (4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(phenyl)iodonium tolsylate 
• 868629-78-1 2-(5-bromo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 935446-54-1 2-(5-iodo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1333492-67-3 2-(2-methoxyphenyl)-4-(3-(pyridin-2-yl)-1-trityl-1H-pyrazol-4-yl)pyridine 
• 395-48-2 1-methoxy-2-(trifluoromethyl)benzene 
• 1417418-31-5 3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole 
• 1417418-35-9 mesityl(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)iodonium(III) tolsylate 

Relevant articles and documents

Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions

We report a metal-organic framework (MOF) supported monoligated phosphine-cobalt complex, which is an active heterogeneous catalyst for aromatic C?H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF?P?Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF?P) with CoCl2 followed by activation with NaEt3BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF?P?Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C?H borylation. Importantly, the attempt to prepare the homogeneous control (Ph3P?Co) using triphenylphosphine was unsuccessful due to the facile disproportionation reactions or intermolecular ligand exchanges in the solution. In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.

METHOD FOR SYNTHESIZING BORONATE ESTER COMPOUND, SODIUM SALT OF BORONATE ESTER COMPOUND, AND METHOD FOR SYNTHESIZING THE SAME

An object is to establish a technology with which a boronate ester compound can be easily and efficiently synthesized at a low cost with a small number of steps without the need for a complex chemical method and reagents that need to be carefully handled. A further object is to establish a sodium salt of a boronate ester compound that is a novel compound and a technology for synthesizing the sodium salt of a boronate ester compound. Provided are a sodium salt of a boronate ester compound and a method for synthesizing a boronate ester compound or a sodium salt of a boronate ester compound that includes reacting, in a reaction solvent, an organic chloride with a dispersion product obtained by dispersing sodium in a dispersion solvent to obtain an organic sodium compound, and reacting the obtained organic sodium compound with a borate ester compound to obtain a boronate ester compound or a sodium salt of a boronate ester compound.

Arene borylation through C–H activation using Cu3(BTC)2 as heterogeneous catalyst

C–H borylation by diborane is an important process to access organoboron compounds. Noble metals, including Ir and Rh-based complexes either in the form of homogeneous or heterogeneous catalysts, have been reported to promote arene C–H borylation. Recently, metal organic frameworks (MOFs) having Ir and Co as active sites have been used as catalysts, but they require co-catalysts. In the present study, commercially available Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) MOF is reported as an effective catalyst to promote borylation of arenes through C–H activation employing bis(pinacolato)diboron (1) as reagent leading to benzylic and aromatic borylation products. Interestingly, other related MOFs like MIL-101(Cr) and Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylate) do not exhibit catalytic activity under identical conditions. Mechanistic studies using in-situ IR spectroscopy reveal that Cu ions play a crucial role in activating the arene and B–B bond in 1.