2-Ethynyl-4-methylpyridine

Base Information

• Chemical Name: 2-Ethynyl-4-methylpyridine
• CAS No.: 30413-54-8
• Molecular Formula: C8H7N
• Molecular Weight: 117.15
• Hs Code.: 2933399090
• European Community (EC) Number: 848-065-1
• DSSTox Substance ID: DTXSID60539548
• Wikidata: Q82415325
• Mol file: 30413-54-8.mol

Synonyms:2-ETHYNYL-4-METHYLPYRIDINE;30413-54-8;Pyridine, 2-ethynyl-4-methyl-;SCHEMBL1460015;DTXSID60539548;MFCD13175245;AKOS006334452;AB66576;BS-35915;CS-0433810;2-ethynyl-4-methylpyridine(SALTDATA: FREE);E84174;EN300-1694130

Chemical Property of 2-Ethynyl-4-methylpyridine

Chemical Property:

• Boiling Point: 102-105 °C(Press: 26 Torr)
• PKA: 2.93±0.20(Predicted)
• PSA: 12.89000
• Density: 1.00±0.1 g/cm3(Predicted)
• LogP: 1.37130
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.057849228
• Heavy Atom Count: 9
• Complexity: 131

Purity/Quality:

97% ^*data from raw suppliers

2-ethynyl-4-methylpyridine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NC=C1)C#C

Technology Process of 2-Ethynyl-4-methylpyridine

There total 6 articles about 2-Ethynyl-4-methylpyridine 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: 99.0%

4-methyl-2-[2-(trimethylsilyl)ethynyl]pyridine (884494-41-1) → 2-ethynyl-4-methylpyridine (30413-54-8)

Guidance literature:

With potassium fluoride; In methanol; at 20 ℃; for 18h;

DOI:10.1021/jacs.6b03842

Reference yield:

2-Bromo-4-picoline (4926-28-7) → 2-ethynyl-4-methylpyridine (30413-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / benzene / 7 h / 50 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / -30 - 0 °C

2.2: 0 °C

With copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; benzene;

Reference yield:

2-chloro-4-picoline (3678-62-4) → 2-ethynyl-4-methylpyridine (30413-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trans-bis(triphenylphosphine)palladium dichloride; copper(l) iodide; triphenylphosphine; diethylamine / N,N-dimethyl-formamide / 0.45 h / 120 °C / Inert atmosphere; Microwave irradiation

2: potassium fluoride / methanol / 18 h / 20 °C

With potassium fluoride; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; diethylamine; triphenylphosphine; In methanol; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1021/jacs.6b03842

upstream raw materials:

2-Bromo-4-picoline

trimethylsilylacetylene

2-methyl-but-3-yn-2-ol

4-methyl-2-[2-(trimethylsilyl)ethynyl]pyridine