2-Bromopyridine-5-boronic acid

Base Information

• Chemical Name: 2-Bromopyridine-5-boronic acid
• CAS No.: 223463-14-7
• Molecular Formula: C5H5BBrNO2
• Molecular Weight: 201.815
• Hs Code.: 29333990
• European Community (EC) Number: 672-028-7
• DSSTox Substance ID: DTXSID70376380
• Nikkaji Number: J1.720.049F
• Wikidata: Q72511837
• ChEMBL ID: CHEMBL3236616
• Mol file: 223463-14-7.mol

Synonyms:2-bromopyridine-5-boronic acid

Chemical Property of 2-Bromopyridine-5-boronic acid

Chemical Property:

• Vapor Pressure: 9.42E-06mmHg at 25°C
• Melting Point: 161-166 °C
• Refractive Index: 1.602
• Boiling Point: 358.2 °C at 760 mmHg
• PKA: 6.62±0.10(Predicted)
• Flash Point: 170.4 °C
• PSA: 53.35000
• Density: 1.78 g/cm³
• LogP: -0.47610
• Storage Temp.: Keep Cold
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 200.95967
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

2-Bromopyridine-5-boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=C(C=C1)Br)(O)O
• Uses: Reactant involved in:Iterative cross-coupling reactions for synthesis of non-cytotoxic terpyridinesThe Garlanding approach for synthesis of phenyl-pyridyl scaffoldsCyanation for synthesis of aromatic nitrilesSuzuki-Miyaura cross-coupling with dihalopyridines and dihalobipyridinesPetasis boronic Mannich reaction

Technology Process of 2-Bromopyridine-5-boronic acid

There total 5 articles about 2-Bromopyridine-5-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: 94.0%

2,5-dibromopyridine (624-28-2) → 6-bromopyridin-3-ylboronic acid (223463-14-7)

Guidance literature:

2,5-dibromopyridine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

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

With water; sodium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.tet.2009.04.049

Reference yield: 72.0%

2,5-dibromopyridine (624-28-2) + Triisopropyl borate (5419-55-6) → 6-bromopyridin-3-ylboronic acid (223463-14-7)

Guidance literature:

2,5-dibromopyridine; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 2h;

Triisopropyl borate; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 2h;

Reference yield: 10.0%

2-bromo-5-iodo-pyridine (73290-22-9) → 6-bromopyridin-3-ylboronic acid (223463-14-7)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(02)00152-7

upstream raw materials:

2,5-dibromopyridine

2-bromo-5-iodo-pyridine

2-aminopyridine

2-amino-5-iodopyridine

Downstream raw materials:

2-bromo-5-phenyl-pyridine

2-(6-bromo-pyridin-3-yl)-pyrimidine

5,6'-dibromo-[2,3']bipyridine

2-bromo-5-(4-bromophenyl)pyridine

Refernces

• 1、 Burzicki, Grégory,Voisin-Chiret, Anne Sophie,Oliveira Santos, Jana Sopkovà-de,Rault, Sylvain. "Synthesis of dihalo bi- and terpyridines by regioselective Suzuki-Miyaura cross-coupling reactions". scheme or table. p. 5413 - 5417. Retrieved 2009/10/24.
• 2、 Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valérie,Bovy, Philippe R,Rault, Sylvain. "Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters". . p. 2885 - 2890. Retrieved 2007/10/03.