3-Biphenylboronic acid

Base Information

• Chemical Name: 3-Biphenylboronic acid
• CAS No.: 5122-95-2
• Molecular Formula: C12H11BO2
• Molecular Weight: 198.029
• Hs Code.: 29163990
• European Community (EC) Number: 671-848-2
• DSSTox Substance ID: DTXSID10370206
• Nikkaji Number: J609.753G
• Wikidata: Q72443633
• ChEMBL ID: CHEMBL20421
• Mol file: 5122-95-2.mol

Synonyms:3-Biphenylboronic acid;5122-95-2;Biphenyl-3-boronic acid;[1,1'-Biphenyl]-3-ylboronic acid;biphenyl-3-ylboronic acid;(3-phenylphenyl)boronic Acid;3-biphenyl boronic acid;MFCD01318102;Boronic acid, [1,1'-biphenyl]-3-yl-;[1,1'-Diphenyl]-3-ylboronic acid;(3-phenylphenyl)boranediol;3-PHENYLBENZENEBORONIC ACID;(1,1'-biphenyl-3-yl)boronic acid;Phenylboronic Acid, 5;Biphenyl-3-bronic acid;3-biphenyl-boronic acid;Biphenyl-3-ylbronic acid;D05GPK;SCHEMBL66838;CHEMBL20421;3-BIPHENYLYLBORONIC ACID;BDBM26126;1,1'-biphenyl-3-ylboronic acid;DTXSID10370206;GOXICVKOZJFRMB-UHFFFAOYSA-N;BBL102079;STL555878;AKOS004116507;{[1,1'-biphenyl]-3-yl}boronic acid;AB08624;CS-W002759;GS-6830;OL10080;AC-24803;SY019960;A7569;AM20050465;B2489;FT-0615110;EN300-197283;J-519853;Z1203159465;3-Biphenylboronic Acid, (contains varying amounts of Anhydride)

Chemical Property of 3-Biphenylboronic acid

Chemical Property:

• Appearance/Colour: yellow crystal powder
• Vapor Pressure: 1.72E-07mmHg at 25°C
• Melting Point: 193-198 °C(lit.)
• Refractive Index: 1.61
• Boiling Point: 411 °C at 760 mmHg
• PKA: 8.30±0.10(Predicted)
• Flash Point: 202.3 °C
• PSA: 40.46000
• Density: 1.18 g/cm³
• LogP: 1.03340
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

3-Biphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)C2=CC=CC=C2)(O)O
• Uses: 3-Biphenylboronic Acid is a fluorescent boronic acid useful for sensitive detection of sugars in water. suzuki reaction It is a biological reagent used as a boronate-assisted fluorogenic chemosensor. It is evaluated for pharmacological activity as fatty acid amide hydrolase inhibitors. It is a reactant involved in coupling with potassium cyanate, quinones, or fluorous tagged N-hydroxyphthalimide and direct C-H arylation of electron-deficient heterocycles. Biological reagent used as a boronate-assisted fluorogenic chemosensorEvaluated for pharmacological activity as fatty acid amide hydrolase inhibitorsReactant involved in:Coupling with potassium cyanate, quinones, or fluorous tagged N-hydroxyphthalimideDirect C-H arylation of electron-deficient heterocycles

Technology Process of 3-Biphenylboronic acid

There total 10 articles about 3-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: 75.0%

Trimethyl borate (121-43-7,63156-11-6) + 3-bromobiphenyl (2113-57-7) → 3-Biphenylboronic acid (5122-95-2)

Guidance literature:

3-bromobiphenyl; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/jp010869j

Reference yield: 55.0%

3-bromobiphenyl (2113-57-7) → 3-Biphenylboronic acid (5122-95-2)

Guidance literature:

3-bromobiphenyl; With n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 1h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; hexane; at -80 - 20 ℃; for 4h;

With hydrogenchloride; water; In tetrahydrofuran; hexane; for 2h;

Reference yield: 40.0%

Trimethyl borate (121-43-7,63156-11-6) + 4-bromo-1,1'-biphenyl (92-66-0) → 3-Biphenylboronic acid (5122-95-2)

Guidance literature:

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; BuLi soln. (hexane) addn. to biphenylbromide soln. (THF), mixt. stirring1 h, mixt. addn. to B-compd. soln. (THF) via canula (N2) at -78° C., stirring 1 h, gradual warming to room temp., aq. HCl addn., stirringat room temp. 15 h, solvent removal; under reduced pressure, Et2O addn., org. layer sepn., drying (MgSO4), soln. concn.. oil triturating with hexane, solid repptn. from MeOH/H2O;

upstream raw materials:

boric acid tributyl ester

[(1,1'-biphenyl)-3-yl]magnesium bromide

Trimethyl borate

3-bromobiphenyl

Downstream raw materials:

4-biphenyl-3-yl-6-chloro-pyrimidin-2-ylamine

C₂₇H₃₃NO₅

C₁₇H₁₂Br₃N

5-(3-biphenyl)-2,3,4-tribromoselenophene

Refernces

• 1、 -. "9H-CARBAZOLE COMPOUNDS AND ELECTROLUMINESCENT DEVICES INVOLVING THEM". Paragraph 129-130. . Retrieved 2013/03/26.
• 2、 Li, Bi-Jie,Tian, Shi-Liang,Fang, Zhao,Shi, Zhang-Jie. "Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components". . p. 1115 - 1118. Retrieved 2008/09/21.