2-Methoxy-5-methylphenylboronic acid

Base Information

• Chemical Name: 2-Methoxy-5-methylphenylboronic acid
• CAS No.: 127972-00-3
• Molecular Formula: C8H11BO3
• Molecular Weight: 165.985
• Hs Code.: 29319090
• European Community (EC) Number: 805-877-0
• DSSTox Substance ID: DTXSID90378487
• Nikkaji Number: J329.353J
• Wikidata: Q72490599
• Mol file: 127972-00-3.mol

Synonyms:2-Methoxy-5-methylphenylboronic acid;127972-00-3;(2-methoxy-5-methylphenyl)boronic acid;2-Methoxy-5-methylbenzeneboronic Acid;Boronic acid, (2-methoxy-5-methylphenyl)-;BORONIC ACID, B-(2-METHOXY-5-METHYLPHENYL)-;5-METHYL-2-METHOXYPHENYLBORONIC ACID;SCHEMBL188250;DTXSID90378487;CSVKZOZMPSRLTC-UHFFFAOYSA-N;2-Methoxy-5-methylphenylboronicacid;MFCD02179465;STK075820;2-methoxy-5-methyl-phenylboronic acid;2-methoxy-5-methylphenyl boronic acid;AKOS000492662;5-methyl-2-methoxybenzene boronic acid;CS-W000836;2-methoxy-5-methyl phenyl boronic acid;2-methoxy-5-methyl-phenyl boronic acid;NCGC00326394-01;DS-12303;FT-0643077;M2311;2-Methoxy-5-methylphenylboronic acid, >=95%;H11347;AB01321332-02;EN300-1232136;A805769;J-509829;Z57206655;F3145-2349;(2-methoxy-5-methyl-phenyl)boronic acid;2-Methoxy-5-methylphenylboronic Acid

Chemical Property of 2-Methoxy-5-methylphenylboronic acid

Chemical Property:

• Vapor Pressure: 2.97E-05mmHg at 25°C
• Melting Point: 92-97 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 342.026 °C at 760 mmHg
• PKA: 8.65±0.58(Predicted)
• Flash Point: 160.652 °C
• PSA: 49.69000
• Density: 1.14 g/cm³
• LogP: -0.31660
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.0801244
• Heavy Atom Count: 12
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxy-5-methylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-60-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC(=C1)C)OC)(O)O
• Uses: Reactant for:Coupling reactionsPreparation of selective quinazolinyl-phenol inhibitors of CHK1 as potential antitumors and radioprotectantsRh-catalyzed asymmetric arylation of aldehydesStereoselective hydroarylation reactionsSuzuki-Miyaura cross-coupling suzuki reaction

Technology Process of 2-Methoxy-5-methylphenylboronic acid

There total 5 articles about 2-Methoxy-5-methylphenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-bromo-4-methylanisole (22002-45-5) → 2-methoxy-5-methylphenyl boronic acid (127972-00-3)

Guidance literature:

2-bromo-4-methylanisole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield: 47.0%

p-methylanizole (104-93-8) + Trimethyl borate (121-43-7,63156-11-6) → 2-methoxy-5-methylphenyl boronic acid (127972-00-3)

Guidance literature:

p-methylanizole; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at 20 ℃; for 12h; Inert atmosphere;

Trimethyl borate; In diethyl ether; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c3dt51240a

Reference yield:

2-bromo-4-methylanisole (22002-45-5) → 2-methoxy-5-methylphenyl boronic acid (127972-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg; I₂ / diethyl ether / 20 °C

1.2: diethyl ether / -80 - 20 °C

2.1: aq. HCl / 20 °C

With hydrogenchloride; iodine; magnesium; In diethyl ether;

DOI:10.1021/ma048144b

upstream raw materials:

2-bromo-4-methylanisole

Trimethyl borate

p-methylanizole

Downstream raw materials:

C₁₉H₁₈O₂

Refernces

• 1、 Mathieu, Véronique,Van Den Berge, Emilie,Ceusters, Justine,Konopka, Tomasz,Cops, Antonin,Bruyère, Céline,Pirker, Christine,Berger, Walter,Trieu-Van, Tran,Serteyn, Didier,Kiss, Robert,Robiette, Rapha?l. "New 5-aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting". . p. 6626 - 6637. Retrieved 2013/10/01.
• 2、 Busico, Vincenzo,Cipullo, Roberta,Friederichs, Nic,Ronca, Sara,Talarico, Giovanni,Togrou, Maria,Wang, Bing. "Block copolymers of highly isotactic polypropylene via controlled Ziegler-Natta polymerization". . p. 8201 - 8203. Retrieved 2007/10/03.