Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylate

Base Information

• Chemical Name: Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylate
• CAS No.: 124558-62-9
• Molecular Formula: C₁₈H₁₆N₂O₈
• Molecular Weight: 388.334
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID90376226
• Wikidata: Q82165097
• Mol file: 124558-62-9.mol

Synonyms:124558-62-9;Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylate;Dimethyl 4-[2,6-bis(methoxycarbonyl)pyridin-4-yl]pyridine-2,6-dicarboxylate;TETRAMETHYL 4,4'-BIPYRIDINE-2,2',6,6'-TETRACARBOXYLATE;2,2',6,6'-Tetrakis(methoxycarbonyl)-4,4'-bipyridine;Oprea1_165782;SCHEMBL9034755;DTXSID90376226;AKOS015909887;FT-0729781;2,2', 6,6'-tetra(methoxycarbonyl)-4,4'-bipyridine;2,2',6,6'-tetra(methoxycarbonyl)-4,4'-bipyridine;Tetramethyl[4,4'-bipyridine]-2,2',6,6'-tetracarboxylate;[4,4'-Bipyridine]-2,2',6,6'-tetracarboxylicacid,2,2',6,6'-tetramethyl ester

Chemical Property of Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylate

Chemical Property:

• Boiling Point: 577.9°Cat760mmHg
• Flash Point: 303.3°C
• PSA: 130.98000
• Density: 1.326g/cm³
• LogP: 1.29000
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 388.09066547
• Heavy Atom Count: 28
• Complexity: 510

Purity/Quality:

98%Min ^*data from raw suppliers

2,2',6,6'-TETRAKIS(METHOXYCARBONYL)-4,4'-BIPYRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=CC(=N1)C(=O)OC)C2=CC(=NC(=C2)C(=O)OC)C(=O)OC

Technology Process of Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylate

There total 6 articles about Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylate 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: 98.0%

methanol (67-56-1) + [4,4'-bipyridine]-2,2',6,6'-tetracarboxylic acid (124558-60-7) → 2,2',6,6'-Tetramethoxycarbonyl-4,4'-bipyridine (124558-62-9)

Guidance literature:

With sulfuric acid; for 4h; Heating;

Reference yield: 88.0%

dimethyl 4-chloro-2,6-pyridinedicarboxylate (5371-70-0) → 2,2',6,6'-Tetramethoxycarbonyl-4,4'-bipyridine (124558-62-9)

Guidance literature:

With bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc; In N,N-dimethyl-formamide; at 70 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03579

Reference yield:

Chelidamic acid (499-51-4) → 2,2',6,6'-Tetramethoxycarbonyl-4,4'-bipyridine (124558-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: P,P-dichlorophenylphosphine oxide / Heating

2: zinc; bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide / N,N-dimethyl-formamide / 0.17 h / 70 °C / Inert atmosphere

With P,P-dichlorophenylphosphine oxide; bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc; In N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.8b03579

upstream raw materials:

methanol

[4,4'-bipyridine]-2,2',6,6'-tetracarboxylic acid

2,6-dimethylpyridine

2,2’,6,6’-tetramethyl-4,4’-bipyridine

Refernces

• 1、 Leone, Loredana,Guarnieri, Luca,Martinelli, Jonathan,Sisti, Massimo,Penoni, Andrea,Botta, Mauro,Tei, Lorenzo. "Rigid and Compact Binuclear Bis-hydrated Gd-complexes as High Relaxivity MRI Agents". supporting information. p. 11811 - 11817. Retrieved 2021/07/09.