Pyridine-3-boronic acid

Base Information

• Chemical Name: Pyridine-3-boronic acid
• CAS No.: 1692-25-7
• Molecular Formula: C5H6BNO2
• Molecular Weight: 122.919
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID30370268
• Nikkaji Number: J806.559D
• Wikipedia: 3-pyridinylboronic acid
• Wikidata: Q72504650
• ChEMBL ID: CHEMBL3236605
• Mol file: 1692-25-7.mol

Synonyms:3-pyridineboronic acid

Chemical Property of Pyridine-3-boronic acid

Chemical Property:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 0.000288mmHg at 25°C
• Melting Point: >300 ºC
• Refractive Index: 1.534
• Boiling Point: 308.8 ºC at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 140.5 ºC
• PSA: 53.35000
• Density: 1.23 g/cm³
• LogP: -1.23860
• Storage Temp.: 0-6°C
• Solubility.: Slightly soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 123.0491586
• Heavy Atom Count: 9
• Complexity: 89

Purity/Quality:

99% ^*data from raw suppliers

3-Pyridineboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,C,F
• Hazard Codes: Xn,Xi,C,F
• Statements: 36/37/38-22-34-11
• Safety Statements: 36/37/39-3-26-45-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=CC=C1)(O)O
• Uses: 3-Pyridylboronic acid is a reagent used for? ;Phosphine-free Suzuki-Miyaura cross-coupling reactions 1 ;Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation 2 ;N-arylation using copper acetylacetonate catalyst 3 ;Copper-mediated cyanation and regioselective cyanation of electron-rich benzenes 4 Reagent use in Preparation of ? ;New linear poly(phenylpyridyl) chains by Suzuki coupling 5 ;Oligopyridyl foldamers as mimics of a-helix twist 6 ;Many highly significant therapeutic enzymatic and kinase inhibitors and r suzuki reaction

Technology Process of Pyridine-3-boronic acid

There total 17 articles about Pyridine-3-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: 98.0%

3-Bromopyridine (626-55-1,163928-56-1) + n-butyllithium (109-72-8,29786-93-4) → 3-pyridylboronic acid (1692-25-7)

Guidance literature:

3-Bromopyridine; n-butyllithium; In toluene; at -50 ℃;

With Triisopropyl borate; In tetrahydrofuran; at -50 - -15 ℃;

DOI:10.1016/S0040-4039(02)00776-1

Reference yield: 75.0%

3-Bromopyridine (626-55-1,163928-56-1) → 3-pyridylboronic acid (1692-25-7)

Guidance literature:

3-Bromopyridine; With isopropylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 2h;

With tris(trimethylsilyl)borate; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

With hydrogenchloride; at 0 ℃; pH=6 - 7;

DOI:10.1081/SCC-120016325

Reference yield: 73.0%

3-Bromopyridine (626-55-1,163928-56-1) + Triisopropyl borate (5419-55-6) → 3-pyridylboronic acid (1692-25-7)

Guidance literature:

3-Bromopyridine; With n-butyllithium; In tetrahydrofuran; hexanes; toluene; at -60 - -50 ℃; for 0.75h;

Triisopropyl borate; With hydrogenchloride; In tetrahydrofuran; hexanes; water; toluene; at -50 - -15 ℃;

upstream raw materials:

3-Bromopyridine

n-butyllithium

lithium methanolate

4'-bromo-2,2':6',2''-terpyridine

Downstream raw materials:

methyl <3,3'-bipyridine>-5-carboxylate

3-(2-methyl-5-nitro-phenyl)-pyridine

3-(3-bromo-5-nitro-phenyl)-pyridine

3-(2-chloro-5-nitro-phenyl)-pyridine