2-Benzyloxyphenylboronic acid

Base Information

• Chemical Name: 2-Benzyloxyphenylboronic acid
• CAS No.: 190661-29-1
• Molecular Formula: C13H13BO3
• Molecular Weight: 228.055
• Hs Code.: 29319090
• European Community (EC) Number: 672-876-8
• DSSTox Substance ID: DTXSID10378308
• Nikkaji Number: J2.119.149C
• Wikidata: Q72442477
• Pharos Ligand ID: KPURRWFMPD9M
• ChEMBL ID: CHEMBL3814113
• Mol file: 190661-29-1.mol

Synonyms:2-Benzyloxyphenylboronic acid;190661-29-1;2-(Benzyloxy)phenylboronic acid;(2-(Benzyloxy)phenyl)boronic acid;2-Benzyloxybenzeneboronic acid;(2-Benzyloxyphenyl)boronic acid;(2-phenylmethoxyphenyl)boronic Acid;[2-(benzyloxy)phenyl]boronic acid;MFCD01632206;Boronic acid, [2-(phenylmethoxy)phenyl]-;CHEMBL3814113;2-(PHENYLMETHOXY)BENZENEBORONIC ACID;2-(PHENYLMETHYL)OXYPHENYLBORONIC ACID;SCHEMBL132403;2-benzyloxyphenyl boronic acid;2-benzyloxyphenyl-boronic acid;(2-benzyloxyphenyl) boronic Acid;DTXSID10378308;MCAIDINWZOCYQK-UHFFFAOYSA-N;2-Phenylmethoxy Phenylboronic Acid;O-BENZYLOXYPHENYLBORONIC ACID;BBL102107;BDBM50180628;STL555906;2-(phenylmethoxy) benzeneboronic acid;AKOS004116106;AB09476;AM86724;AS-2616;CS-T-06181;CS-W002801;NCGC00249541-01;SY014627;A4203;B4590;Boronic acid, B-[2-(phenylmethoxy)phenyl]-;FT-0611319;EN300-822201;Q-102197;F0001-0687;Z381512972

Chemical Property of 2-Benzyloxyphenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white Powder
• Vapor Pressure: 4.13E-08mmHg at 25°C
• Melting Point: 105-110 °C(lit.)
• Refractive Index: 1.593
• Boiling Point: 428.7 °C at 760 mmHg
• PKA: 8.57±0.53(Predicted)
• Flash Point: 213 °C
• PSA: 49.69000
• Density: 1.2 g/cm³
• LogP: 0.94540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 228.0957744
• Heavy Atom Count: 17
• Complexity: 217

Purity/Quality:

98% ^*data from raw suppliers

2-(Benzyloxy)phenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1OCC2=CC=CC=C2)(O)O
• Uses: 2-Benzyloxyphenylboronic acid is a reagent used in the preparation of different kinase inhibitors. Palladium complex-catalyzed selective hydroxylation ? Palladium(II)-catalyzed oxidative Heck reactions ? Metal-free electrophilic fluorination ? Suzuki-Miyaura cross-coupling reactions Reactant for:? ;Palladium complex-catalyzed selective hydroxylation1? ;Palladium(II)-catalyzed oxidative Heck reactions2? ;Metal-free electrophilic fluorination3? ;Suzuki-Miyaura cross-coupling reactions4 suzuki reaction

Technology Process of 2-Benzyloxyphenylboronic acid

There total 15 articles about 2-Benzyloxyphenylboronic 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: 63.3%

boric acid tributyl ester (688-74-4) + 2-bromophenyl benzyl ether (31575-75-4) → 2-benzyloxyphenylboronic acid (190661-29-1)

Guidance literature:

2-bromophenyl benzyl ether; With iodine; magnesium; In tetrahydrofuran; at 47 ℃; for 2h; Inert atmosphere;

boric acid tributyl ester; In tetrahydrofuran; at -30 - 20 ℃; for 4h; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.3184/174751915X14418863197125

Reference yield: 63.0%

2-bromophenyl benzyl ether (31575-75-4) → 2-benzyloxyphenylboronic acid (190661-29-1)

Guidance literature:

2-bromophenyl benzyl ether; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h;

DOI:10.1021/ol0479904

Reference yield:

Triisopropyl borate (5419-55-6) + 2-bromophenyl benzyl ether (31575-75-4) → 2-benzyloxyphenylboronic acid (190661-29-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane;

upstream raw materials:

2-bromophenyl benzyl ether

2-hydroxybromobenzene

benzyl chloride

Triisopropyl borate

Downstream raw materials:

2-(2-benzyloxyphenyl)-4-bromothiophene

2'-benzyloxy-3-chloro-2-nitrobiphenyl

2'-benzyloxy-2-nitrobiphenyl

methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

Refernces

• 1、 -. "Method for preparing azoxystrobin on basis of Suzuki reaction". . . Retrieved 2016/10/10.
• 2、 Hall, Adrian,Brown, Susan H.,Budd, Christopher,Clayton, Nicholas M.,Giblin, Gerard M.P.,Goldsmith, Paul,Hayhow, Thomas G.,Hurst, David N.,Naylor, Alan,Anthony Rawlings,Scoccitti, Tiziana,Wilson, Alexander W.,Winchester, Wendy J.. "Discovery of GSK345931A: An EP1 receptor antagonist with efficacy in preclinical models of inflammatory pain". scheme or table. p. 497 - 501. Retrieved 2011/03/18.