2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Base Information

• Chemical Name: 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 269410-25-5
• Molecular Formula: C14H21BO3
• Molecular Weight: 248.13
• Hs Code.: 29310099
• European Community (EC) Number: 671-675-2
• DSSTox Substance ID: DTXSID20370419
• Wikidata: Q82157606
• Mol file: 269410-25-5.mol

Synonyms:269410-25-5;2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;4-Hydroxy-3,5-dimethylphenylboronic acid pinacol ester;3,5-Dimethy-4-hydroxyphenylboronic acid pinacol ester;3,5-dimethyl-4-hydroxybenzeneboronic acid, pinacol ester;3,5-Dimethyl-4-hydroxyphenylboronic acid pinacol ester;3,5-DIMETHYL-4-HYDROXYPHENYLBORONIC ACID, PINACOL ESTER;MFCD02093724;SCHEMBL177571;4-hydroxy-3,5-dimethylphenylboronic acid, pinacol ester;DTXSID20370419;TYCKOBOJYNRIBO-UHFFFAOYSA-N;2,6-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2,6-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol;2,6-dimethyl-4-(4,4-5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;AKOS015894338;AB10819;PS-9710;AM807676;CS-0089478;D2853;FT-0644224;T70695;2,6-dimethylphenol-4-boronic acid pinacol ester;EN300-7361147;A818727;J-016626;Z1741960588;4-Hydroxy-3,5-dimethylphenylboronic acid pinacol ester, 97%;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-xylenol;2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol;2-(4-Hydroxy-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Chemical Property:

• Appearance/Colour: White to beige crystalline powder
• Vapor Pressure: 6.51E-06mmHg at 25°C
• Melting Point: 100-105 °C(lit.)
• Refractive Index: 1.512
• Boiling Point: 367.3 °C at 760 mmHg
• PKA: 10.36±0.40(Predicted)
• Flash Point: 176 °C
• PSA: 38.69000
• Density: 1.06 g/cm³
• LogP: 2.30820
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: Insoluble in water
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 248.1583747
• Heavy Atom Count: 18
• Complexity: 288

Purity/Quality:

97% ^*data from raw suppliers

3,5-Dimethyl-4-hydroxyphenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C(=C2)C)O)C
• Uses: 3,5-Dimethyl-4-hydroxyphenylboronic acid, pinacol ester

Technology Process of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

There total 3 articles about 2,6-Dimethyl-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:

4-bromo-2,6-dimethyl-phenol (2374-05-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (269410-25-5)

Guidance literature:

With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; for 18h;

4-bromo-2,6-dimethyl-phenol; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With triethylamine; In 1,4-dioxane; at 100 ℃; for 336h;

Reference yield:

4-bromo-2,6-dimethyl-phenol (2374-05-2) → 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (269410-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: [{Pd(μ-Cl){κ²-P,C-P(iPr)₂(OC₆H₃-2-Ph)}}₂]; sodium acetate / dichloromethane; water / 6 h / 40 °C / Inert atmosphere

2: ethyl acetate / 40 °C

With [{Pd(μ-Cl){κ²-P,C-P(iPr)₂(OC₆H₃-2-Ph)}}₂]; sodium acetate; In dichloromethane; water; ethyl acetate;

DOI:10.1021/acs.joc.7b02771

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-hydroxy-3,5-dimethylphenylboronic acid (934826-20-7) → 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (269410-25-5)

Guidance literature:

In ethyl acetate; at 40 ℃;

DOI:10.1021/acs.joc.7b02771

upstream raw materials:

4-bromo-2,6-dimethyl-phenol

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2,3-dimethyl-2,3-butane diol

4-hydroxy-3,5-dimethylphenylboronic acid

Downstream raw materials:

4-(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)-2,6-dimethylphenol

bis(3,5-dimethyl-4-hydroxy)phenyl-3,3'-dipentoxy-2,2'-bithiophene

Refernces

• 1、 -. "Hydroboronation process". Page column 68. . Retrieved 2010/02/05.