2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 144432-80-4
• Molecular Formula: C18H21 B O2
• Molecular Weight: 280.175
• Hs Code.: 29319090
• European Community (EC) Number: 671-857-1
• ChEMBL ID: CHEMBL1952307
• DSSTox Substance ID: DTXSID60475311
• Nikkaji Number: J3.040.309F
• Pharos Ligand ID: AC1YPV3ZFVHA
• Wikidata: Q82305746
• Mol file: 144432-80-4.mol

Synonyms:144432-80-4;4-Biphenylboronic acid pinacol ester;2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-BIPHENYLBORONIC ACID, PINACOL ESTER;2-(4-Biphenylyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(4-phenylphenyl)-1,3,2-dioxaborolane;1,3,2-DIOXABOROLANE, 2-[1,1'-BIPHENYL]-4-YL-4,4,5,5-TETRAMETHYL-;CHEMBL1952307;MFCD07368291;Biphenyl-4-boronic acid pinacol ester;4-Methylphentlboronic acid pinacol ester;4-BIPHENYLBORONIC ACID,PINACOL ESTER;SCHEMBL476870;Pinacol(4-Phenylphenyl)Boronate;4-Biphenylboronicacidpinacolester;DTXSID60475311;2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl;BDBM50364295;AKOS015951042;AB32014;CS-W000872;AM808130;AS-18691;SY037936;B3019;FT-0686865;4-Biphenylboronic acid pinacol ester, AldrichCPR;EN300-1425720;A808215;[1,1'-BIPHENYL]-4-YLBORONIC ACID PINACOL ESTER;Z1336745159;2-(biphenyl-2-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 112 °C
• Refractive Index: 1.549
• Boiling Point: 396°Cat760mmHg
• Flash Point: 193.3°C
• PSA: 18.46000
• Density: 1.05g/cm³
• LogP: 3.65280
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 280.1634601
• Heavy Atom Count: 21
• Complexity: 336

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C3=CC=CC=C3
• Uses: It is an important raw material and intermediate used in organic synthesis and pharmaceuticals. 4-Biphenylboronic Acid, Pinacol Ester is a useful intermediate for organic synthesis and an important raw material for pharmaceuticals. suzuki reaction

Technology Process of 2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 119 articles about 2-([1,1'-Biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-biphenylboronic acid (5122-94-1) → 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4)

Guidance literature:

With potassium phosphate; water; In tetrahydrofuran; at 90 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201500970

Reference yield: 95.0%

4-bromo-1,1'-biphenyl (92-66-0) + bis(pinacol)diborane (73183-34-3) → 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4)

Guidance literature:

bis(pinacol)diborane; With (Bis(tri-tert-butylphosphine)palladium⁽⁰⁾); SPGS-550-M; NOK; potassium acetate; In water; for 0.166667h; Inert atmosphere; Sealed tube;

4-bromo-1,1'-biphenyl; With SPGS-550-M; NOK; In water; for 24h; Reagent/catalyst; Inert atmosphere; Sealed tube;

DOI:10.1021/jo401744b

Reference yield: 93.0%

4-iodo-biphenyl (1591-31-7) + bis(pinacol)diborane (73183-34-3) → 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4)

Guidance literature:

bis(pinacol)diborane; With potassium ethoxide; C₄₀H₆₂N₄Zn₂; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique;

4-iodo-biphenyl; In tetrahydrofuran; at 75 ℃; for 3h; Inert atmosphere; Glovebox; Schlenk technique;

DOI:10.1021/acs.organomet.0c00733

upstream raw materials:

bis(pinacol)diborane

4,4″-sulfinyldi-1,1′-biphenyl

4-phenylphenyl triflate

biphenyl-4-carboxylic acid

Downstream raw materials:

4-Phenylphenol

biphenyl-4-yl-phenyl-methanone

3-bromo-p-terphenyl

4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl

Refernces

• 1、 Mohan, Balaji,Kang, Hyuntae,Park, Kang Hyun. "Phosphine and palladium-free synthesis of aryl and alkenyl boronates: A nano-catalytic approach". . p. 61 - 65. Retrieved 2016.
• 2、 Ji, Shuohan,Qin, Shengxiang,Yin, Chunyu,Luo, Lu,Zhang, Hua. "Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation". supporting information. p. 64 - 68. Retrieved 2021/12/27.
• 3、 -. "Preparation method of aryl borate catalyzed by cesium neovalerate". Paragraph 0030-0033; 0066-0067. . Retrieved 2021/09/22.