3-(Hydroxymethyl)phenylboronic acid

Base Information

• Chemical Name: 3-(Hydroxymethyl)phenylboronic acid
• CAS No.: 87199-15-3
• Molecular Formula: C7H9BO3
• Molecular Weight: 151.958
• Hs Code.: 29319090
• European Community (EC) Number: 672-931-6
• DSSTox Substance ID: DTXSID00370432
• Nikkaji Number: J2.225.064G
• Wikidata: Q72485466
• ChEMBL ID: CHEMBL349516
• Mol file: 87199-15-3.mol

Synonyms:Boronicacid, [3-(hydroxymethyl)phenyl]- (9CI);(m-Hydroxymethyl)phenylboronic acid;3-Hydroxymethylbenzeneboronic acid;3-(Hydroxymethyl)phenylboronic acid;

Chemical Property of 3-(Hydroxymethyl)phenylboronic acid

Chemical Property:

• Appearance/Colour: off-white cryst
• Vapor Pressure: 1.82E-06mmHg at 25°C
• Melting Point: 95-99 °C(lit.)
• Refractive Index: 1.566
• Boiling Point: 380.5 °C at 760 mmHg
• PKA: 8.31±0.10(Predicted)
• Flash Point: 183.9 °C
• PSA: 60.69000
• Density: 1.25 g/cm³
• LogP: -1.14130
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.0644743
• Heavy Atom Count: 11
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)CO)(O)O
• Uses: suzuki reaction Reactant used for copper-mediated trifluoromethylation, copper-catalyzed transformations from arylboronic acids in water, Mitsunobu, Suzuki, and amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate. Reactant involved in the synthesis of biologically active molecules including Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors via Suzuki coupling reactions, HIV protease inhibitors with antiviral activity against drug-resistant viruses, Pyrrole derivatives for use as PDE4B inhibitors.

Technology Process of 3-(Hydroxymethyl)phenylboronic acid

There total 4 articles about 3-(Hydroxymethyl)phenylboronic 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: 98.0%

n-butyllithium (109-72-8,29786-93-4) + Trimethyl borate (121-43-7,63156-11-6) + (3-Bromophenyl)methanol (15852-73-0) → [3-(hydroxymethyl)phenyl]boronic acid (87199-15-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; hexane;

Reference yield: 75.0%

Triisopropyl borate (5419-55-6) + [(3-bromobenzyl)oxy](tert-butyl)dimethylsilane (103978-12-7) → [3-(hydroxymethyl)phenyl]boronic acid (87199-15-3)

Guidance literature:

[(3-bromobenzyl)oxy](tert-butyl)dimethylsilane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

Triisopropyl borate; In tetrahydrofuran; at 20 ℃; for 2.83h;

Reference yield:

(3-Bromophenyl)methanol (15852-73-0) → [3-(hydroxymethyl)phenyl]boronic acid (87199-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 2 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

2.2: 2.83 h / 20 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; dichloromethane;

upstream raw materials:

n-butyllithium

Trimethyl borate

(3-Bromophenyl)methanol

Triisopropyl borate

Downstream raw materials:

[3-(2-amino-6-chloro-pyrimidin-4-yl)-phenyl]-methanol

7-(3-(hydroxymethyl) phenyl)-1-phenyl-5-trifluoromethylbenzimidazole

{3-[9-(1-benzylpiperidin-4-yl)-6-morpholin-4-yl-9H-purin-2-yl]phenyl}methanol

Refernces

• 1、 Richter, Jeremy M.,Cheney, Daniel L.,Bates, J. Alex,Wei, Anzhi,Luettgen, Joseph M.,Rendina, Alan R.,Harper, Timothy M.,Narayanan, Rangaraj,Wong, Pancras C.,Seiffert, Dietmar,Wexler, Ruth R.,Priestley, E. Scott. "Design and synthesis of novel meta-linked phenylglycine macrocyclic FVIIa inhibitors". . p. 67 - 72. Retrieved 2017/12/12.
• 2、 -. "Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa". . . Retrieved 2008/06/13.