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

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 269409-70-3
• Molecular Formula: C12H17BO3
• Molecular Weight: 220.076
• Hs Code.: 29319090
• European Community (EC) Number: 627-688-0
• DSSTox Substance ID: DTXSID70370404
• Nikkaji Number: J2.278.414E
• Wikidata: Q72480986
• Mol file: 269409-70-3.mol

Synonyms:269409-70-3;4-Hydroxyphenylboronic acid pinacol ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;4-hydroxyphenylboronic acid, pinacol ester;MFCD02093756;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;PHENOL, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;4-Hydroxyphenylboronic acid pinacol cyclic ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol;2-(4-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(4-HYDROXYPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL102562;4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenol;DTXSID70370404;BICZJRAGTCRORZ-UHFFFAOYSA-N;AKOS015915429;AB10835;AS-2606;CS-W002879;PB42436;SY020873;4-hydroxybenzene boronic acid pinacol ester;AM20060974;FT-0644217;T1954;4-Hydroxyphenylboronic acid pinacol ester, 97%;EN300-316486;A818720;J-016615;Z1741960628;4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-)phenol;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2yl)phenol;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)phenol;4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)phenol;4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenol;4-[4,4,5,5tetramethyl-1,3,2-dioxaborolan-2-yl]-phenol;4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-) phenol;4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenol;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol

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

Chemical Property:

• Appearance/Colour: yellow to light brown crystalline powder
• Vapor Pressure: 6.87E-05mmHg at 25°C
• Melting Point: 113-117 °C(lit.)
• Refractive Index: 1.514
• Boiling Point: 333.23°C at 760 mmHg
• PKA: 9.61±0.30(Predicted)
• Flash Point: 155.691 °C
• PSA: 38.69000
• Density: 1.088 g/cm³
• LogP: 1.69140
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Acetonitrile, DMSO, Methanol
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 220.1270746
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)O
• Uses: 4-Hydroxyphenylboronic acid pinacol ester is widely used in Suzuki coupling chemistry. suzuki reaction Widely used in Suzuki coupling chemistry.

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

There total 39 articles about 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: 100.0%

4,4,5,5-tetramethyl-2-(4-trimethylsilanyloxy-phenyl)-[1,3,2]dioxaborolane → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-70-3)

Guidance literature:

With sulfuric acid; at 0 ℃; pH=5;

DOI:10.1002/adsc.200202198

Reference yield: 99.0%

4-chloro-phenol (106-48-9,82344-39-6) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-70-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; XPhos; In 1,4-dioxane; at 110 ℃; for 1h; Inert atmosphere;

Reference yield: 98.2%

4-bromo-phenol (106-41-2) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-70-3)

Guidance literature:

With palladium diacetate; triphenylphosphine; cesium pivalate; In 1,4-dioxane; at 90 ℃; for 3h; Inert atmosphere;

upstream raw materials:

p-Iodophenol

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

4-chloro-phenol

bis(pinacol)diborane

Downstream raw materials:

2-(4-hydroxyphenyl)-4-(3-pyridin-2-yl-1-trityl-1H-pyrazol-4-yl)pyridine

4-(2-( 4-( 4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine

isoquinoline-1-carboxylic acid [4'-hydroxy-4-piperazin-1-yl-6-(2-trifluoromethyl-phenoxymethyl)-biphenyl-3-yl]-amide

4-[(2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Refernces

• 1、 Cao, Jilei,Tang, Xinxin,Toh, Ren Wei,Wang, Han,Wu, Jie,Wu, Xiangyang,Xu, Jinhui,Yang, Xiaona,Yeow, Edwin K. L.,Zhou, Rong. "Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides". supporting information. p. 13266 - 13273. Retrieved 2021/09/07.
• 2、 -. "Liquid crystal phosphorescent material based on cyclometalated complex and application thereof". Paragraph 0019-0020; 0028-0029. . Retrieved 2021/06/09.