2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Base Information

• Chemical Name: 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 269410-22-2
• Molecular Formula: C13H19BO4
• Molecular Weight: 250.102
• Hs Code.: 29310099
• European Community (EC) Number: 628-175-4
• DSSTox Substance ID: DTXSID30370420
• Nikkaji Number: J2.152.801C
• Wikidata: Q82157608
• Mol file: 269410-22-2.mol

Synonyms:269410-22-2;2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;4-Hydroxy-3-methoxyphenylboronic acid pinacol ester;4-hydroxy-3-methoxyphenylboronic acid, pinacol ester;MFCD02093723;PHENOL, 2-METHOXY-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol;4-Hydroxy-3-methoxybenzeneboronic acid, pinacol ester;SCHEMBL9401;2-methoxy-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;DTXSID30370420;WFSJROCEOJANPD-UHFFFAOYSA-N;(4-HYDROXY-3-METHOXYPHENYL)BORONIC ACID PINACOL ESTER;2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol;AKOS005256839;AS-3284;AM803612;BP-12811;2-Methoxyphenol-4-boronic acid pinacol ester;CS-0036776;FT-0644222;EN300-268995;A818726;J-016623;Z1741960599;4-Hydroxy-3-methoxyphenylboronic acid pinacol ester, 98%;methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2-(4-hydroxy-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan;2-Methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yI)-phenol;2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol;2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenol

Chemical Property of 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Chemical Property:

• Appearance/Colour: white to cream crystalline powder
• Vapor Pressure: 6.5E-06mmHg at 25°C
• Melting Point: 105-109 °C(lit.)
• Refractive Index: 1.512
• Boiling Point: 367.3 °C at 760 mmHg
• PKA: 9.66±0.35(Predicted)
• Flash Point: 176 °C
• PSA: 47.92000
• Density: 1.11 g/cm³
• LogP: 1.70000
• Storage Temp.: Refrigerator (+4°C)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 250.1376392
• Heavy Atom Count: 18
• Complexity: 289

Purity/Quality:

97% ^*data from raw suppliers

4-Hydroxy-3-methoxyphenylboronic acid,pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)O)OC
• Uses: 4-Hydroxy-3-methoxyphenylboronic acid, pinacol ester 4-Hydroxy-3-methoxyphenylboronic acid pinacol ester can be used as a reactant: In the Suzuki-Miyaura cross-coupling reaction. To prepare ethylidenedihydroindolones as potential neoplastic agents. To synthesize 5,6-dihydropyrrolo[2,1-b]isoquinoline derivatives, which can be utilized as scaffolds to prepare lamellarin analogs via regioselective bromination and Suzuki cross-coupling reactions.

Technology Process of 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

There total 7 articles about 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 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: 66.7%

4-bromoguaiacol (7368-78-7) + bis(pinacol)diborane (73183-34-3) → 4-hydroxy-3-methoxyphenylboronic acid pinacol ester (269410-22-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; ethanol; at 90 ℃; for 16h;

Reference yield: 36.0%

(E)-2-methoxy-4-(1-(((perfluorobenzoyl)oxy)imino)ethyl)phenyl acetate + bis(pinacol)diborane (73183-34-3) → 4-hydroxy-3-methoxyphenylboronic acid pinacol ester (269410-22-2)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; palladium dichloride; In 1,2-dichloro-ethane; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.202006740

Reference yield:

C11H13NO4 → 4-hydroxy-3-methoxyphenylboronic acid pinacol ester (269410-22-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube

2: palladium dichloride; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube

With pyridine; 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; palladium dichloride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/anie.202006740

upstream raw materials:

4-bromoguaiacol

bis(pinacol)diborane

2-methoxy-phenol

4-acetyl-2-methoxyphenyl acetate

Downstream raw materials:

methyl 1-(4-hydroxy-3-methoxyphenyl)-8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

1,2-bis-(4-hydroxy-3-methoxy-phenyl)-8-isopropoxy-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid methyl ester