Ethyl 2,6-bis(6-methylpyridin-2-yl)pyridine-4-carboxylate

Base Information

• Chemical Name: Ethyl 2,6-bis(6-methylpyridin-2-yl)pyridine-4-carboxylate
• CAS No.: 372520-84-8
• Molecular Formula: C20H19N3O2
• Molecular Weight: 333.38400
• DSSTox Substance ID: DTXSID70376421
• Nikkaji Number: J1.561.829I
• Wikidata: Q82165351
• Mol file: 372520-84-8.mol

Synonyms:372520-84-8;Ethyl 2,6-bis(6-methylpyridin-2-yl)pyridine-4-carboxylate;6,6''-Dimethyl-[2,2':6',2''-terpyridine]-4'-carboxylic acid ethyl ester;Ethyl-6,6''-dimethyl-2,2':6',2''-terpyridin-4'-carboxylat;DTXSID70376421;FT-0620839;J-400959;Ethyl 6,6''-dimethyl-[2,2':6',2''-terpyridine]-4'-carboxylate;Ethyl 6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylate;Ethyl6,6''-dimethyl-[2,2':6',2''-terpyridine]-4'-carboxylate;6,6''-Dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester;6,6-DIMETHYL-[2,2:6,2-TERPYRIDINE]-4-CARBOXYLICACIDETHYLESTER;Ethyl 1~6~,3~6~-dimethyl[1~2~,2~2~:2~6~,3~2~-terpyridine]-2~4~-carboxylate

Chemical Property of Ethyl 2,6-bis(6-methylpyridin-2-yl)pyridine-4-carboxylate

Chemical Property:

• Boiling Point: 483.9oC at 760 mmHg
• Flash Point: 246.5oC
• PSA: 64.97000
• Density: 1.163g/cm3
• LogP: 3.99910
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 333.147726857
• Heavy Atom Count: 25
• Complexity: 415

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

6,6''-DIMETHYL-[2,2':6',2''-TERPYRIDINE]-4'-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=NC(=C1)C2=CC=CC(=N2)C)C3=CC=CC(=N3)C

Technology Process of Ethyl 2,6-bis(6-methylpyridin-2-yl)pyridine-4-carboxylate

There total 4 articles about Ethyl 2,6-bis(6-methylpyridin-2-yl)pyridine-4-carboxylate 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: 63.0%

2,6-dichloroisonicotinic acid ethyl ester (1604-14-4) + 2-methyl-6-(tributylstannyl)pyridine (259807-95-9) → 6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester (372520-84-8)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 72h; Heating;

DOI:10.1021/jo0480242

Reference yield: 55.0%

ethyl 2,6-dibromo-pyridine-4-carboxylate (90050-70-7) + 2-methyl-6-(tributylstannyl)pyridine (259807-95-9) → 6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester (372520-84-8)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 48h; Heating;

DOI:10.1055/s-2002-33347

Reference yield:

citrazinic acid (99-11-6) → 6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester (372520-84-8)

Guidance literature:

Multi-step reaction with 3 steps

1: POBr₃ / 3 h / 180 °C

2: H₂SO₄

3: 44 percent / Pd(PPh₃)4 / toluene / 48 h / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; phosphorus(V) oxybromide; In toluene; 3: Stille cross-coupling;

DOI:10.1016/S0040-4039(01)01195-9

upstream raw materials:

ethyl 2,6-dibromo-pyridine-4-carboxylate

2-methyl-6-(tributylstannyl)pyridine

2,6-dichloroisonicotinic acid ethyl ester

citrazinic acid

Downstream raw materials:

ethyl 6,6''-bis-(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylate