5-Methylpyridine-3-boronic acid

Base Information

• Chemical Name: 5-Methylpyridine-3-boronic acid
• CAS No.: 173999-18-3
• Molecular Formula: C6H8BNO2
• Molecular Weight: 136.946
• Hs Code.: 2933399090
• European Community (EC) Number: 690-413-8
• DSSTox Substance ID: DTXSID90376382
• Wikidata: Q72496515
• Mol file: 173999-18-3.mol

Synonyms:Boronicacid, (5-methyl-3-pyridinyl)- (9CI);(3-Methyl-5-pyridyl)boronic acid;(5-Methylpyridin-3-yl)boronic acid;Boronic acid, B-(5-methyl-3-pyridinyl)-;

Chemical Property of 5-Methylpyridine-3-boronic acid

Chemical Property:

• Vapor Pressure: 6.03E-05mmHg at 25°C
• Melting Point: >300℃
• Refractive Index: 1.527
• Boiling Point: 331.9 °C at 760 mmHg
• PKA: 4.10±0.10(Predicted)
• Flash Point: 154.5 °C
• PSA: 53.35000
• Density: 1.18 g/cm³
• LogP: -0.93020
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 137.0648087
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

5-Methylpyridine-3-boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CN=C1)C)(O)O
• Uses: suzuki reaction

Technology Process of 5-Methylpyridine-3-boronic acid

There total 1 articles about 5-Methylpyridine-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:

5-bromo-3-picoline (3430-16-8) → 5-methylpyridine-3-boronic acid (173999-18-3)

Guidance literature:

5-bromo-3-picoline; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h;

With Triisopropyl borate; In diethyl ether; hexane; at -78 ℃; for 1h;

With water; In diethyl ether; hexane; at -78 - 20 ℃;

Reference yield: 100.0%

(3R,4R)-tert-butyl 4-((2-(benzyloxy)-5-bromo-3-methyl-1,7-naphthyridin-8-yl)amino)-3-((4,4-difluorocyclohexyl)methoxy)piperidine-1-carboxylate + 5-methylpyridine-3-boronic acid (173999-18-3) → (3R,4R)-tert-butyl 4-((2-(benzyloxy)-3-methyl-5-(5-methylpyridin-3-yl)-1,7-naphthyridin-8-yl)amino)-3-((4,4-difluorocyclohexyl)methoxy)piperidine-1-carboxylate

Guidance literature:

With palladium diacetate; potassium carbonate; catacxium A; In 1,4-dioxane; water; at 100 ℃; for 1h; Microwave irradiation;

DOI:10.1002/anie.201603928

Reference yield: 93.0%

(1S*,2S*,3R*,5R*)-tert-butyl 3-((2-(benzyloxy)-5-bromo-3-methyl-1,7-naphthyridin-8-yl)amino)-2-(2-(4,4-difluorocyclohexyl)ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate + 5-methylpyridine-3-boronic acid (173999-18-3) → (1S*,2S*,3R*,5R*)-tert-butyl 3-((2-(benzyloxy)-3-methyl-5-(5-methylpyridin-3-yl)-1,7-naphthyridin-8-yl)amino)-2-(2-(4,4-difluorocyclohexyl)ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Guidance literature:

With di(adamantan-1-yl)(butyl)phosphine; palladium diacetate; potassium carbonate; In 1,4-dioxane; water; at 100 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acs.jmedchem.8b00862

upstream raw materials:

5-bromo-3-picoline

Downstream raw materials:

methyl 5'-methyl-5-(1,3-thiazol-2-yl)-2,3'-bipyridine-4-carboxylate

2-(5-methylpyridin-3-yl)-N-phenyl-4-[(2-pyridin-2-ylethyl)amino]-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxamide

trans-4-(4-(5-methyl-pyridin-3-yl)-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide

C₁₉H₂₀N₄O

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