3-Benzyloxybenzeneboronic Acid

Base Information

• Chemical Name: 3-Benzyloxybenzeneboronic Acid
• CAS No.: 156682-54-1
• Molecular Formula: C13H13BO3
• Molecular Weight: 228.055
• Hs Code.: 29310095
• European Community (EC) Number: 674-523-3
• DSSTox Substance ID: DTXSID90370204
• Wikidata: Q72441759
• Mol file: 156682-54-1.mol

Synonyms:156682-54-1;3-Benzyloxyphenylboronic acid;3-Benzyloxybenzeneboronic Acid;(3-(Benzyloxy)phenyl)boronic acid;3-(Benzyloxy)phenylboronic acid;(3-phenylmethoxyphenyl)boronic Acid;MFCD02093063;M-BENZYLOXYPHENYLBORONIC ACID;[3-(benzyloxy)phenyl]boronic acid;3-Benzyloxy-phenylboronic acid;Boronic acid, [3-(phenylmethoxy)phenyl]-;(3-benzyloxyphenyl)boronic acid;Boronic acid, B-[3-(phenylmethoxy)phenyl]-;SCHEMBL22315;3-Benzyloxyphenyl Boronic Acid;3-benzyloxy-benzeneboronic acid;3-benzyloxy-phenyl boronic acid;3-(Benzyloxy)benzeneboronic acid;3-(benzyloxy)phenyl boronic acid;DTXSID90370204;WIJNYNBSPQMJGO-UHFFFAOYSA-N;3-Benzyloxyphenylboronic acid, 97%;AKOS004116107;AB10742;AS-2469;CS-W014695;NCGC00249493-01;NCGC00249493-02;3-(Benzyloxy)phenylboronic acid, >=95%;AC-24826;BP-12101;SY020991;A3441;AM20050284;B3056;FT-0615103;EN300-345407;J-511766;F0001-0557;Z381513308

Chemical Property of 3-Benzyloxybenzeneboronic Acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 4.3E-08mmHg at 25°C
• Melting Point: 125-130 °C(lit.)
• Refractive Index: 1.593
• Boiling Point: 428.159 °C at 760 mmHg
• PKA: 8.10±0.10(Predicted)
• Flash Point: 212.743 °C
• PSA: 49.69000
• Density: 1.202 g/cm³
• LogP: 0.94540
• Storage Temp.: 0-6°C
• Water Solubility.: Slightly soluble in water
• 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:

99% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)OCC2=CC=CC=C2)(O)O
• Uses: Reactant for:? ;Microwave Suzuki-Miyaura coupling1? ;Preparation of palladium-based fluoride-derived electrophilic fluorination reagent for PET imaging agents2? ;Synthesis of substituted isoindolines via palladium-catalyzed cascade reaction3? ;Ruthenium-catalyzed hydrogenation4? ;Suzuki coupling reactions5 suzuki reaction Reactant for:Microwave Suzuki-Miyaura couplingPreparation of palladium-based fluoride-derived electrophilic fluorination reagent for PET imaging agentsSynthesis of substituted isoindolines via palladium-catalyzed cascade reactionRuthenium-catalyzed hydrogenationSuzuki coupling reactions

Technology Process of 3-Benzyloxybenzeneboronic Acid

There total 10 articles about 3-Benzyloxybenzeneboronic 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: 95.0%

2-(3-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (765908-38-1) → 3-(benzyloxy)phenylboronic acid (156682-54-1)

Guidance literature:

With hydrogenchloride; polystyrene boronic acid; In acetonitrile;

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 66.0%

3-(benzyloxy)phenyl bromide (53087-13-1) → 3-(benzyloxy)phenylboronic acid (156682-54-1)

Guidance literature:

3-(benzyloxy)phenyl bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; hexane; Inert atmosphere;

DOI:10.1039/b923267b

Reference yield:

3-(benzyloxy)phenyl bromide (53087-13-1) + Triisopropyl borate (5419-55-6) → 3-(benzyloxy)phenylboronic acid (156682-54-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

upstream raw materials:

2-(3-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

3-(benzyloxy)phenyl bromide

tri-n-propyl borate

Triisopropyl borate

Downstream raw materials:

3'-benzyloxy-5-nitro-biphenyl-2-carboxylic acid benzyl ester

2-[3-(3-benzyloxy-phenoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

5-(benzyloxy)-2-iodophenylboronic acid

3-(3'-benzyloxybiphenyl-3-yl)propionic acid

Refernces

• 1、 -. "With anti-tumor activity of a biphenyl amide compound and its preparation method and application". Paragraph 0047; 0048; 0049. . Retrieved 2016/10/07.
• 2、 Lu, Wen,Li, Pengfei,Shan, Yuanyuan,Su, Ping,Wang, Jinfeng,Shi, Yaling,Zhang, Jie. "Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies". . p. 1044 - 1054. Retrieved 2015/03/04.