4-Benzyloxyphenylboronic acid

Base Information

• Chemical Name: 4-Benzyloxyphenylboronic acid
• CAS No.: 146631-00-7
• Molecular Formula: C13H13BO3
• Molecular Weight: 228.055
• Hs Code.: 29310095
• European Community (EC) Number: 678-070-2
• DSSTox Substance ID: DTXSID50370205
• Nikkaji Number: J1.141.265C
• Wikidata: Q72441763
• ChEMBL ID: CHEMBL1824170
• Mol file: 146631-00-7.mol

Synonyms:4-Benzyloxyphenylboronic acid;146631-00-7;4-Benzyloxybenzeneboronic Acid;(4-(Benzyloxy)phenyl)boronic acid;4-(Benzyloxy)phenylboronic acid;(4-phenylmethoxyphenyl)boronic Acid;[4-(benzyloxy)phenyl]boronic acid;MFCD01075705;4-Benzyloxy-phenylboronic acid;Boronic acid, [4-(phenylmethoxy)phenyl]-;(4-benzyloxyphenyl)boronic acid;4-benzoxyphenylboronic acid;SCHEMBL142665;4-Benzyloxyphenyl boronic acid;4-benzyloxybenzene boronic acid;CHEMBL1824170;4-benzyloxy benzene boronic acid;DTXSID50370205;DMJHEIDWSIAXCS-UHFFFAOYSA-N;4-(phenylmethoxy)phenylboronic acid;[4-(Benzyloxy)phenyl]-boronic acid;4-(phenylmethoxy)benzeneboronic acid;|N-BENZYLOXYPHENYLBORONIC ACID;AKOS004116470;AB08171;AS-2468;CS-W000873;[4-(phenylmethoxy)phenyl]-boronic acid;NCGC00249494-01;AC-24815;AM808104;SY014624;{4-[(phenylmethyl)oxy]phenyl}boronic acid;4-(Benzyloxy)phenylboronic acid, >=95.0%;B2145;Boronic acid, B-[4-(phenylmethoxy)phenyl]-;FT-0617663;A22910;EN300-384084;J-514507;Z381513140

Chemical Property of 4-Benzyloxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 9.1E-08mmHg at 25°C
• Melting Point: 198-200 °C
• Refractive Index: 1.593
• Boiling Point: 418.9 °C at 760 mmHg
• PKA: 8.70±0.16(Predicted)
• Flash Point: 207.2 °C
• PSA: 49.69000
• Density: 1.2 g/cm³
• LogP: 0.94540
• Storage Temp.: 0-6°C
• Solubility.: Chloroform, DMSO, Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 228.0957744
• Heavy Atom Count: 17
• Complexity: 209

Purity/Quality:

99% ^*data from raw suppliers

4-Benzyloxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XiC
• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)OCC2=CC=CC=C2)(O)O
• Uses: suzuki reaction It is used as electronic intermediate. It is also utilized in HPLC and NMR spectroscopy. 4-Benzyloxybenzeneboronic Acid is a reagent in the synthesis of arylalkenylpropargylamines as neuroprotective and potent selective monoamine oxidase B inhibitors. Also used to prepare pyridone alkaloids used as antiproliferative agents.

Technology Process of 4-Benzyloxyphenylboronic acid

There total 16 articles about 4-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: 92.1%

p-benzyloxyphenylbromide (6793-92-6) → [4-(benzyloxy)phenyl]boronic acid (146631-00-7)

Guidance literature:

With Trimethyl borate; sulfuric acid; iodine; magnesium; In tetrahydrofuran; at -40 - 20 ℃; for 2h; Heating / reflux;

Reference yield: 86.0%

p-benzyloxyphenylbromide (6793-92-6) + Trimethyl borate (121-43-7,63156-11-6) → [4-(benzyloxy)phenyl]boronic acid (146631-00-7)

Guidance literature:

p-benzyloxyphenylbromide; With iodine; magnesium; In tetrahydrofuran; for 0.75h; Heating;

Trimethyl borate; In tetrahydrofuran; at -78 ℃; for 1h;

With hydrogenchloride; at 20 ℃; for 1h;

DOI:10.1080/744815207

Reference yield: 25.0%

tetrahydroxydiboron (13675-18-8) + p-benzyloxyaniline (6373-46-2) → [4-(benzyloxy)phenyl]boronic acid (146631-00-7)

Guidance literature:

p-benzyloxyaniline; With hydrogenchloride; In water; at 20 ℃; for 0.0166667h;

With sodium nitrite; In water; at 0 ℃; for 0.25h;

tetrahydroxydiboron; With sodium acetate; In water; at 20 ℃; for 0.333333h;

DOI:10.1021/jo501665e

upstream raw materials:

p-benzyloxyphenylbromide

Trimethyl borate

4-bromo-phenol

benzyl bromide

Downstream raw materials:

2-(4-benzyloxy-phenyl)-5-trifluoromethyl-pyridine

4'-benzyloxy-4-biphenylferrocene

Refernces

• 1、 Panda, Gautam,Srinivas Lavanya Kumar. "Versatile synthesis of 4-aryl chroman and 1-aryl tetralins through metal-free reductive arylations". . p. 753 - 758. Retrieved 2019.
• 2、 -. "Preparation method of trans-ketone intermediate". Paragraph 0068-0072; 0074. . Retrieved 2021/06/06.
• 3、 Munteanu, Charissa,Spiller, Taylor E.,Qiu, Jun,Delmonte, Albert J.,Wisniewski, Steven R.,Simmons, Eric M.,Frantz, Doug E.. "Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4". . p. 10334 - 10349. Retrieved 2020/09/18.