4-Benzyloxy-2-methylphenylboronic acid

Base Information

• Chemical Name: 4-Benzyloxy-2-methylphenylboronic acid
• CAS No.: 847560-49-0
• Molecular Formula: C14H15 B O3
• Molecular Weight: 242.082
• Hs Code.: 29310095
• European Community (EC) Number: 813-609-9
• DSSTox Substance ID: DTXSID70378304
• Wikidata: Q72442424
• Mol file: 847560-49-0.mol

Synonyms:4-Benzyloxy-2-methylphenylboronic acid;847560-49-0;(4-Benzyloxy-2-methylphenyl)boronic acid;(2-methyl-4-phenylmethoxyphenyl)boronic acid;4-BENZYLOXY-2-METHYLBENZENEBORONIC ACID;MFCD03788404;[4-(benzyloxy)-2-methylphenyl]boronic acid;SCHEMBL539890;DTXSID70378304;VCDFDGOVNBMYRW-UHFFFAOYSA-N;AMY28889;BBL100663;STL554457;4-Benzyloxy-2-methylphenylboronicacid;2-methyl-4-benzyloxyphenylboronic acid;AKOS004119260;AB15963;CS-W010277;AS-17797;FT-0644903;N12046;A840905;J-514498;[2-(benzyloxymethyl)phenyl]boronic acid

Chemical Property of 4-Benzyloxy-2-methylphenylboronic acid

Chemical Property:

• Vapor Pressure: 2.22E-08mmHg at 25°C
• Melting Point: 154-158
• Boiling Point: 436.2°C at 760 mmHg
• PKA: 8.78±0.58(Predicted)
• Flash Point: 217.6°C
• PSA: 49.69000
• Density: 1.17g/cm³
• LogP: 1.25380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.1114245
• Heavy Atom Count: 18
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

4-Benzyloxy-2-methylphenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=C(C=C1)OCC2=CC=CC=C2)C)(O)O
• Uses: suzuki reaction 4-Benzyloxy-2-methylphenylboronic Acid is used in the development of Phenyl-oxazoles, a family of H3R inverse agonists that exhibits anti-amnesic effects.

Technology Process of 4-Benzyloxy-2-methylphenylboronic acid

There total 4 articles about 4-Benzyloxy-2-methylphenylboronic 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: 92.0%

4-(benzyloxy)-1-bromo-2-methylbenzene (17671-75-9) → [4-(benzyloxy)-2-methylphenyl]boronic acid (847560-49-0)

Guidance literature:

4-(benzyloxy)-1-bromo-2-methylbenzene; With para-bromotoluene; magnesium; ethylene dibromide; In diethyl ether; at 35 ℃; for 2h; Inert atmosphere;

With boric acid tributyl ester; In diethyl ether; at 5 ℃; for 2h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;

Reference yield:

C16H19BO3 → [4-(benzyloxy)-2-methylphenyl]boronic acid (847560-49-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

DOI:10.1002/1521-3765(20001016)6:20<3821::AID-CHEM3821>3.0.CO;2-8

Reference yield:

4-bromo-3-methylphenol (14472-14-1) → [4-(benzyloxy)-2-methylphenyl]boronic acid (847560-49-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 77 percent / K₂CO₃ / acetone / 8 h / Heating

2.1: BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: tetrahydrofuran; hexane / -78 - 20 °C

3.1: 6.5 g / aq. HCl / tetrahydrofuran; hexane / 1 h / 0 °C

With hydrogenchloride; n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; acetone; 1.1: Etherification / 2.1: Metallation / 2.2: Substitution / 3.1: Hydrolysis;

DOI:10.1002/1521-3765(20001016)6:20<3821::AID-CHEM3821>3.0.CO;2-8

upstream raw materials:

4-bromo-3-methylphenol

4-(benzyloxy)-1-bromo-2-methylbenzene

benzyl bromide

Downstream raw materials:

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

2-((2S,4S)-1-(4-(4-(benzyloxy)-2-methylphenoxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

C₂₃H₂₆N₂O₂

4-[2'-Methyl-4'-(3-methylbenzyloxy)biphenyl-4-yloxymethyl]-2,2-dimethyl-1,3-dioxolane

Refernces

• 1、 Koelbel, Marius,Beyersdorff, Tom,Tschierske, Carsten,Diele, Siegmar,Kain, Jens. "Thermotropic and lyotropic liquid crystalline phases of rigid aromatic amphiphiles". . p. 3821 - 3837. Retrieved 2007/10/03.