4-Methoxy-2,6-dimethylphenylboronic acid

Base Information

• Chemical Name: 4-Methoxy-2,6-dimethylphenylboronic acid
• CAS No.: 361543-99-9
• Molecular Formula: C9H13BO3
• Molecular Weight: 180.011
• Hs Code.: 29319090
• European Community (EC) Number: 689-088-5
• DSSTox Substance ID: DTXSID00395428
• Nikkaji Number: J2.219.309K
• Wikidata: Q72470865
• Mol file: 361543-99-9.mol

Synonyms:361543-99-9;4-Methoxy-2,6-dimethylphenylboronic acid;2,6-Dimethyl-4-Methoxyphenylboronic Acid;(2,6-DIMETHYL-4-METHOXYPHENYL)BORONIC ACID;(4-Methoxy-2,6-dimethylphenyl)boronic acid;2,6-Dimethyl-4-methoxybenzeneboronic acid;4-methoxy-2,6-dimethylphenylboronicacid;Boronic acid, (4-methoxy-2,6-dimethylphenyl)-;MFCD03452755;4-Methoxy-2,6-dimethylbenzeneboronic Acid;(4-methoxy-2,6-dimethyl-phenyl)boronic acid;SCHEMBL1326006;DTXSID00395428;AMY14548;BCP27100;AKOS004116251;AB15464;CS-W017242;DS-1362;A6271;BB 0261948;FT-0644511;M2244;EN300-255839;3H-SPIRO(1-BENZOFURAN-2,3-PYRROLIDINE);J-515629;Z1201622348

Chemical Property of 4-Methoxy-2,6-dimethylphenylboronic acid

Chemical Property:

• Vapor Pressure: 2.2E-05mmHg at 25°C
• Melting Point: 168-172 °C
• Refractive Index: 1.517
• Boiling Point: 346.3 °C at 760 mmHg
• PKA: 9.11±0.58(Predicted)
• Flash Point: 163.2 °C
• PSA: 49.69000
• Density: 1.11 g/cm³
• LogP: -0.00820
• Storage Temp.: Keep Cold
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 180.0957744
• Heavy Atom Count: 13
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dimethyl-4-methoxyphenylboronicacid ^*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=C(C=C1C)OC)C)(O)O
• Uses: suzuki reaction 4-Methoxy-2,6-dimethylbenzeneboronic acid is used as pharmaceutical intermediate.

Technology Process of 4-Methoxy-2,6-dimethylphenylboronic acid

There total 5 articles about 4-Methoxy-2,6-dimethylphenylboronic 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: 83.0%

2-bromo-5-methoxy-1,3-dimethyl-benzene (6267-34-1) → 4-methoxy-2,6-dimethylphenylboronic acid (361543-99-9)

Guidance literature:

2-bromo-5-methoxy-1,3-dimethyl-benzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

DOI:10.1021/ol051365x

Reference yield: 83.0%

Triisopropyl borate (5419-55-6) + 2-bromo-5-methoxy-1,3-dimethyl-benzene (6267-34-1) + ammonium chloride → 4-methoxy-2,6-dimethylphenylboronic acid (361543-99-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate;

Reference yield: 73.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-bromo-5-methoxy-1,3-dimethyl-benzene (6267-34-1) + water (7732-18-5) → 4-methoxy-2,6-dimethylphenylboronic acid (361543-99-9)

Guidance literature:

With CH₃CH₂CH₂CH₂Li; In tetrahydrofuran; hexane; (Ar); addn. of 2.5 M soln. of butyllithium in hexanes to THF soln. of manisyl bromide at -78°C, stirring for 20 min at -78°C, addn. of boron compd., stirring overnight at room temp.; quenching with aq. HCl and water, stirring for 6 h at room temp., addn. of diethyl ether, washing with water, separating organic layer, drying over MgSO4, filtration, evapn., NMR and HRMS;

DOI:10.1039/b804106g

upstream raw materials:

2-bromo-5-methoxy-1,3-dimethyl-benzene

4-bromo-3,5-dimethylphenol

Trimethyl borate

water

Downstream raw materials:

6-(4-methoxy-2,6-dimethyl-phenyl)-8-methyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

4-(4-methoxy-2,6-dimethylphenyl)-3,5-dimethyl-pyridin-1-ol

4-(4-methoxy-2,6-dimethylphenyl)-3,5-dimethyl-pyridine

4-(3,5-dimethylpyridin-4-yl)-3,5-dimethyl-phenol