2-Biphenylboronic acid

Base Information

• Chemical Name: 2-Biphenylboronic acid
• CAS No.: 4688-76-0
• Molecular Formula: C12H11BO2
• Molecular Weight: 198.029
• Hs Code.: 29310095
• European Community (EC) Number: 670-315-1
• ChEMBL ID: CHEMBL467355
• DSSTox Substance ID: DTXSID20404607
• Nikkaji Number: J666.429F
• Wikidata: Q72443637
• Mol file: 4688-76-0.mol

Synonyms:2-Biphenylboronic acid;4688-76-0;Biphenyl-2-boronic acid;(2-phenylphenyl)boronic Acid;biphenyl-2-ylboronic acid;2-Biphenylboronicacid;[1,1'-biphenyl]-2-ylboronic acid;MFCD00136929;2-BIPHENYLYLBORONIC ACID;1,1'-biphenyl-2-boronic acid;(2-Phenylphenyl)Boranediol;Biphenyl-2-bronic acid;Boronic acid, [1,1'-biphenyl]yl-;2-PHENYLBENZENEBORONIC ACID;m-biphenylboronic acid;o-biphenylboronic acid;p-biphenylboronic acid;m-biphenyl boronic acid;Phenylboronic acid, 24;Biphenyl-2-ylbronic acid;2-phenylbenzene boronic acid;(biphenyl-2-yl)boronic acid;SCHEMBL21933;CHEMBL467355;BDBM26137;DTXSID20404607;HYCYKHYFIWHGEX-UHFFFAOYSA-N;AKOS004116075;AB03772;AC-1956;B-[1,1'-Biphenyl]-2-ylboronic acid;CS-W000939;HY-W000939;DS-13664;SY033281;(1,1'-BIPHENYL-2-YL)BORONIC ACID;A7252;AM20060969;B2488;Biphenylboronic acid;Biphenyl-2-boronic Acid;FT-0611324;EN300-1457842;J-519852;Z1255450311;3-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-BENZOICACID

Chemical Property of 2-Biphenylboronic acid

Chemical Property:

• Appearance/Colour: off-white powder
• Melting Point: 167-172 °C(lit.)
• Boiling Point: 404 °C at 760 mmHg
• PKA: 8.50±0.58(Predicted)
• Flash Point: 198.1 °C
• PSA: 40.46000
• Density: 1.18 g/cm³
• LogP: 1.03340
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 198.0852098
• Heavy Atom Count: 15
• Complexity: 190

Purity/Quality:

98% ^*data from raw suppliers

2-Biphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi,Xn
• Hazard Codes: C,Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-60-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C2=CC=CC=C2)(O)O
• Uses: suzuki reaction Reactant involved in:Suzuki-Miyaura cross-coupling reactions with arylhalides, dibromovinyl precursors, alkenyl tosylates and mesylates, and quinoline carboxylatesIntramolecular Friedel-Crafts alkylation for synthesis of chiral tetralinsHydroxylation to phenolsOxidative coupling iwth alkynes

Technology Process of 2-Biphenylboronic acid

There total 16 articles about 2-Biphenylboronic acid 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: 94.0%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + 2-Bromobiphenyl (2052-07-5) → 2-Biphenylboronic acid (4688-76-0)

Guidance literature:

diisopropylamine borane; With magnesium; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

2-Bromobiphenyl; In tetrahydrofuran; at 70 ℃;

methanol; Further stages;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 89.0%

2-Bromobiphenyl (2052-07-5) → 2-Biphenylboronic acid (4688-76-0)

Guidance literature:

2-Bromobiphenyl; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 1h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol2016252

Reference yield: 85.5%

Trimethyl borate (121-43-7,63156-11-6) + 2-Bromobiphenyl (2052-07-5) → 2-Biphenylboronic acid (4688-76-0)

Guidance literature:

2-Bromobiphenyl; With n-butyllithium; In tetrahydrofuran; at -65 - -50 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; at -50 - -5 ℃; for 1h; Reagent/catalyst; Temperature;

upstream raw materials:

boric acid tributyl ester

biphenyl-2-ylmagnesium iodide

2-Bromobiphenyl

Trimethyl borate

Downstream raw materials:

1-([1,1'-biphenyl]-2-yl)-2-methoxynaphthalene

2-(2-biphenylyl)-9,10-anthraquinone

3,6-bis[(1,1’-biphenyl)-2-yl]carbazole

(C₆H₁₁)3PAuC₆H₄(C₆H₅)

Refernces

• 1、 Chang, Junbiao,Dong, Zhenzhen,Li, Xingwei,Liu, Bingxian,Yang, Lingyun. "Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes". . p. 7199 - 7204. Retrieved 2021/09/22.
• 2、 Gao, Wen-Xia,Huang, Xiao-Bo,Liu, Miao-Chang,Wu, Hua-Yue,Zhang, Xue,Zhou, Yun-Bing. "Ag-Catalyzed Cyclization of Arylboronic Acids with Elemental Selenium for the Synthesis of Selenaheterocycles". supporting information. p. 5639 - 5644. Retrieved 2020/11/30.