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

Base Information

• Chemical Name: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 269409-97-4
• Molecular Formula: C12H17BO3
• Molecular Weight: 220.076
• Hs Code.: 29319090
• European Community (EC) Number: 671-854-5
• DSSTox Substance ID: DTXSID50370402
• Wikidata: Q82157589
• Mol file: 269409-97-4.mol

Synonyms:269409-97-4;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2-Hydroxyphenylboronic acid pinacol ester;2-hydroxyphenylboronic acid, pinacol ester;MFCD02093754;2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)phenol;phenol, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-Hydroxybenzeneboronic acid pinacol ester;(2-HYDROXYPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL333869;DTXSID50370402;VLROJECCXBBKPZ-UHFFFAOYSA-N;2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol;2-(2-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;AKOS015950769;AB10830;AS-3008;CS-W008935;SY025275;2-Hydroxyphenyl boronic acid pinacol ester;AM20040060;FT-0644219;T1952;2-Hydroxyphenylboronic acid pinacol ester, 98%;EN300-303427;F14959;A818721;J-016616;4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl-phenol;Z1741960626;2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2-(4,4,5,5,-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol;2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2yl)-phenol;2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenol;2-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)phenol;(2-hydroxyphenyl)-(2-hydroxy-1,1,2-trimethyl-propoxy)borinic acid

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

Chemical Property:

• Appearance/Colour: pale yellow to brown liquid
• Vapor Pressure: 0.000164mmHg at 25°C
• Refractive Index: n20/D 1.506(lit.)
• Boiling Point: 320.9 °C at 760 mmHg
• PKA: 10.17±0.35(Predicted)
• Flash Point: 147.9 °C
• PSA: 38.69000
• Density: 1.09 g/cm³
• LogP: 1.69140
• Storage Temp.: Refrigerator
• 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

2-Hydroxyphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2O
• Uses: 2-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)phenol can be widely used in Suzuki coupling chemistry. Reactant involved in:Synthesis of indolo-fused heterocyclic inhibitors of polymerase enzyme of hepatitis CStudies of pi-interactions, electronic structure and transient UV absorption of subphthalocyanine-borate-bridged ferrocene-fullerene conjugatesSynthesis of subphthalocyanine and fused-ring nicotine derivativesSuzuki-Miyaura coupling-triflation sequence, reduction and salt formation for synthesis of hydroxylated oligoarene phosphines

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

There total 22 articles about 2-(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: 93.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-hydroxyphenyl boronic acid (89466-08-0) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4)

Guidance literature:

In toluene; at 130 ℃; for 25h; Dean-Stark; Inert atmosphere;

DOI:10.1002/anie.201303659

Reference yield: 92.0%

2-fluorophenol (367-12-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4)

Guidance literature:

With 2-((2,4,6-trimethylphenyl)amino)-4-((2,4,6-trimethylphenyl)imino)-2-pentene; magnesium; cobalt(II) chloride; In tetrahydrofuran; at 60 ℃; for 48h; Inert atmosphere; Glovebox;

DOI:10.1021/acs.orglett.8b03167

Reference yield: 83.0%

4,4,5,5-tetramethyl-2-(2-((methylthio)methoxy)phenyl)-1,3,2-dioxaborolane → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4)

Guidance literature:

With iodine; In methanol; at 55 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02936

upstream raw materials:

2-Iodophenol

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

2-amino-phenol

bis(pinacol)diborane

Downstream raw materials:

2-hydroxyphenyl boronic acid

2-(2-chloro-pyridin-3-yl)-phenol

[(4-ferrocenylphenolato)B(C₂₄H₉N₆(C₆H₄OH)3)]

1-carbomethoxy-11-oxatricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene

Refernces

• 1、 Dong, Yunhui,Du, Xin,Li, Xinling,Liu, Hui,Liu, Qing,Wang, Ping,Zhang, Daopeng,Zhang, Lizhi,Zhao, Huan. "Ligand-Regulated Palladium-Catalyzed Regiodivergent Hydroarylation of the Distal Double Bond of Allenamides with Aryl Boronic Acid". . p. 13276 - 13288. Retrieved 2021/10/12.
• 2、 Homma, Yuki,Fukuda, Kazuishi,Iwasawa, Nobuharu,Takaya, Jun. "Ruthenium-catalyzed regio- And site-selective: Ortho C-H borylation of phenol derivatives". . p. 10710 - 10713. Retrieved 2020/10/02.