2-Methoxypyridine-3-boronic acid

Base Information

• Chemical Name: 2-Methoxypyridine-3-boronic acid
• CAS No.: 163105-90-6
• Molecular Formula: C6H8BNO3
• Molecular Weight: 152.945
• Hs Code.: 29339900
• European Community (EC) Number: 672-925-3
• DSSTox Substance ID: DTXSID50376383
• Nikkaji Number: J1.909.711K
• Wikidata: Q72485724
• ChEMBL ID: CHEMBL3236609
• Mol file: 163105-90-6.mol

Synonyms:2-Methoxypyridine-3-boronic acid;163105-90-6;2-Methoxy-3-pyridineboronic acid;(2-methoxypyridin-3-yl)boronic Acid;2-Methoxy-3-pyridylboronic Acid;2-methoxypyridin-3-yl-3-boronic acid;2-Methoxy-3-pyridinyl boronic acid;2-methoxy-3-pyridinylboronic acid;2-methoxypyridin-3-ylboronic acid;Boronic acid, (2-methoxy-3-pyridinyl)-;(2-methoxy-3-pyridyl)boronic acid;MFCD03411572;Boronic acid, B-(2-methoxy-3-pyridinyl)-;SCHEMBL4794;2-methoxypyridyl boronic acid;2-Methoxy-3-pyridineboronicacid;2-methoxypyrid-3-ylboronic acid;CHEMBL3236609;DTXSID50376383;2-methoxy-pyridin-3-boronic acid;NVOLYUXUHWBCRJ-UHFFFAOYSA-N;2-methoxy-3-pyridine boronic acid;2-methoxy-pyridine-3-boronic acid;2-methoxypyridine-3-ylboronic acid;BCP12132;CS-D1050;AKOS002670072;AB14155;AC-2581;GS-6745;(2-(methoxy)pyridin-3-yl)boronic acid;(2-methoxy-pyridin-3-yl)-boronic acid;[2-(methyloxy)-3-pyridinyl]boronic acid;BP-11890;SY002212;AM20050861;FT-0604637;M2159;2-Methoxy-3-pyridinylboronic acid, >=95.0%;A25316;EN300-121455;J-509874;Z1741962386;2-Methoxypyridin-3-ylboronic acid;2-Methoxypyridin-3-ylboronic acid hydrate

Chemical Property of 2-Methoxypyridine-3-boronic acid

Chemical Property:

• Vapor Pressure: 8.78E-05mmHg at 25°C
• Melting Point: 136-138 °C
• Refractive Index: 1.523
• Boiling Point: 326.4 °C at 760 mmHg
• PKA: 6.90±0.58(Predicted)
• Flash Point: 151.2 °C
• PSA: 62.58000
• Density: 1.24 g/cm³
• LogP: -1.23000
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 153.0597233
• Heavy Atom Count: 11
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxypyridine-3-boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(N=CC=C1)OC)(O)O

Technology Process of 2-Methoxypyridine-3-boronic acid

There total 4 articles about 2-Methoxypyridine-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: 68.0%

2-methoxypyridine (1628-89-3) → 2-methoxypyridin-3-yl-boronic acid (163105-90-6)

Guidance literature:

2-methoxypyridine; With trimethylsilylmethyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -20 ℃; for 7h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -20 - 20 ℃; for 0.666667h;

With hydrogenchloride; sodium hydroxide; water; more than 3 stages;

Reference yield: 65.0%

3-Bromo-2-methoxypyridine (13472-59-8) → 2-methoxypyridin-3-yl-boronic acid (163105-90-6)

Guidance literature:

3-Bromo-2-methoxypyridine; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 0.5h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol2016252

Reference yield:

3-Bromo-2-methoxypyridine (13472-59-8) + Trimethyl borate (121-43-7,63156-11-6) → 2-methoxypyridin-3-yl-boronic acid (163105-90-6)

Guidance literature:

3-Bromo-2-methoxypyridine; With magnesium; lithium chloride; In tetrahydrofuran; at 35 ℃; for 2h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at 0 - 35 ℃; for 2h;

upstream raw materials:

2-methoxypyridine

3-iodo-2-methoxypyridine

3-Bromo-2-methoxypyridine

Trimethyl borate

Downstream raw materials:

N-(4-fluoro-2-(2-methoxypyridin-3-yl)benzyl)-3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide

benzyl 2-methoxy-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate

2-amino-4-(2-methoxypyridin-3-yl)phenylamine

2-methoxy-3-cyanopyridine

Refernces

• 1、 Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise. "Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges". supporting information; experimental part. p. 4479 - 4481. Retrieved 2011/10/09.
• 2、 Thompson, Amy E.,Hughes, Gregory,Batsanov, Andrei S.,Bryce, Martin R.,Parry, Paul R.,Tarbit, Brian. "Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: Synthesis of highly substituted bipyridines and pyrazinopyridines". . p. 388 - 390. Retrieved 2007/10/03.