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

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 214360-76-6
• Molecular Formula: C12H17BO3
• Molecular Weight: 220.076
• Hs Code.: 29319090
• European Community (EC) Number: 627-498-8
• DSSTox Substance ID: DTXSID10370403
• Wikidata: Q82157592
• Mol file: 214360-76-6.mol

Synonyms:214360-76-6;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;3-Hydroxyphenylboronic acid pinacol ester;3-hydroxyphenylboronic acid, pinacol ester;Phenol, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;MFCD02093755;3-hydroxybenzeneboronic acid, pinacol ester;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;(3-HYDROXYPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL177535;DTXSID10370403;MUKIFYQKIZOYKT-UHFFFAOYSA-N;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol;2-(3-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;AKOS005254529;AM62758;AS-2490;CS-W005864;3-hydroxybenzeneboronic acid pinacol ester;SY003748;3-hydroxyphenyl-boronic acid pinacol ester;FT-0615856;T1953;3-Hydroxyphenylboronic acid pinacol ester, 97%;EN300-264438;A815369;J-014068;Z1741960627;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol

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

Chemical Property:

• Appearance/Colour: light brown crystalline powder
• Vapor Pressure: 3.51E-05mmHg at 25°C
• Melting Point: 94-98 °C(lit.)
• Refractive Index: 1.514
• Boiling Point: 343.559 °C at 760 mmHg
• PKA: 10.01±0.10(Predicted)
• Flash Point: 161.579 °C
• PSA: 38.69000
• Density: 1.088 g/cm³
• LogP: 1.69140
• 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: 220.1270746
• Heavy Atom Count: 16
• Complexity: 249

Purity/Quality:

98% ^*data from raw suppliers

3-Hydroxyphenylboronic 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:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)O

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

There total 9 articles about 3-(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: 98.0%

3-Bromophenol (591-20-8) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (214360-76-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 85 ℃; for 8h; Inert atmosphere;

Reference yield: 94.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-hydroxyphenylboronic acid (87199-18-6) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (214360-76-6)

Guidance literature:

In dichloromethane; at 20 ℃; for 48h; Time;

Reference yield: 93.0%

2-(3-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (765908-38-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (214360-76-6)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/j.tetlet.2004.07.014

upstream raw materials:

2-(3-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

3-hydroxyphenylboronic acid

3-Bromophenol

Downstream raw materials:

3-[2(R)-tert-butoxycarbonylamino-2-phenylethyl]-5-(3-hydroxyphenyl)-1-[2-bromo-6-fluorobenzyl]-6-methylpyrimidine-2,4(1H,3H)-dione

2-(3-(2-methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

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

Refernces

• 1、 Montero Bastidas, Jose R.,Oleskey, Thomas J.,Miller, Susanne L.,Smith, Milton R.,Maleczka, Robert E.. "Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions". supporting information. p. 15483 - 15487. Retrieved 2019/10/11.
• 2、 -. "Preparation method of (3-(3-(dimethylamino) propoxy) phenyl) boronic acid". Paragraph 0035; 0036. . Retrieved 2017/10/10.