(6-phenylpyridin-3-yl)boronic Acid

Base Information

• Chemical Name: (6-phenylpyridin-3-yl)boronic Acid
• CAS No.: 155079-10-0
• Molecular Formula: C11H10BNO2
• Molecular Weight: 199.017
• Hs Code.: 2933399090
• European Community (EC) Number: 856-504-3
• DSSTox Substance ID: DTXSID10376384
• Wikidata: Q82165329
• Mol file: 155079-10-0.mol

Synonyms:155079-10-0;(6-phenylpyridin-3-yl)boronic Acid;6-PHENYLPYRIDINE-3-BORONIC ACID;2-Phenylpyridine-5-boronic acid;6-Phenylpyridin-3-ylboronic acid;2-Phenyl-pyridine-5-boronic acid;MFCD03788243;(6-Phenylpyridin-3-yl)boronicacid;4-chlorophenylacrylate;SCHEMBL441703;6-Phenylpyridine-3-boronicacid;6-phenyl-3-pyridinylboronic acid;DTXSID10376384;XSQUPVXOENTCJV-UHFFFAOYSA-N;AMY17921;AKOS005256307;AB15948;BS-2016;Boronic acid,(6-phenyl-3-pyridinyl)-(9ci);CS-0190055;FT-0613347;F16117;EN300-7562801;A809606;J-510267

Chemical Property of (6-phenylpyridin-3-yl)boronic Acid

Chemical Property:

• Vapor Pressure: 3.73E-07mmHg at 25°C
• Refractive Index: 1.614
• Boiling Point: 401.1 °C at 760 mmHg
• Flash Point: 196.4 °C
• PSA: 53.35000
• Density: 1.24 g/cm³
• LogP: 0.42840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 199.0804587
• Heavy Atom Count: 15
• Complexity: 195

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Phenylpyridine-3-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=C(C=C1)C2=CC=CC=C2)(O)O

Technology Process of (6-phenylpyridin-3-yl)boronic Acid

There total 4 articles about (6-phenylpyridin-3-yl)boronic 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: 85.79%

Triisopropyl borate (5419-55-6) + 5-bromo-2-phenylpyridine (27012-25-5) → (6-phenylpyridin-3-yl)boronic acid (155079-10-0)

Guidance literature:

5-bromo-2-phenylpyridine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

Reference yield: 73.0%

triethyl borate (150-46-9) + water (7732-18-5) + 5-bromo-2-phenylpyridine (27012-25-5) → (6-phenylpyridin-3-yl)boronic acid (155079-10-0)

Guidance literature:

5-bromo-2-phenylpyridine; With n-butyllithium; In diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

triethyl borate; In diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

water; With hydrogenchloride; In diethyl ether; for 0.5h; Inert atmosphere;

Reference yield:

phenylboronic acid (98-80-6) → (6-phenylpyridin-3-yl)boronic acid (155079-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile; methanol / 18 h / 50 °C / Inert atmosphere

2.1: n-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere

2.2: 4 h / -78 - 20 °C / Inert atmosphere

2.3: 0.5 h / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In methanol; diethyl ether; acetonitrile;

upstream raw materials:

Triisopropyl borate

5-bromo-2-phenylpyridine

triethyl borate

water

Downstream raw materials:

5-(2-nitrophenyl)-2-phenylpyridine

Refernces

• 1、 -. "ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME". Paragraph 0246; 0247; 0250; 0251. . Retrieved 2019/10/23.
• 2、 -. "Metal complex as well as preparation method thereof and application thereof in organic light-emitting devices". Paragraph 0081; 0082; 0083; 0084. . Retrieved 2017/10/14.