DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE

Base Information

• Chemical Name: DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE
• CAS No.: 142593-07-5
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.26
• European Community (EC) Number: 811-042-1
• DSSTox Substance ID: DTXSID60467115
• Nikkaji Number: J1.452.024D
• Wikidata: Q82293920
• Mol file: 142593-07-5.mol

Synonyms:DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE;6,6'-diMethoxycarbonyl-2,2'-bipyridine

Chemical Property of DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE

Chemical Property:

• Melting Point: gt. 192.0 and le 196.0 °C
• Boiling Point: 470.5±45.0 °C(Predicted)
• PKA: 1.19±0.10(Predicted)
• Flash Point: 238.332oC
• PSA: 78.38000
• Density: 1.254±0.06 g/cm3(Predicted)
• LogP: 1.71680
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 272.07970687
• Heavy Atom Count: 20
• Complexity: 327

Purity/Quality:

98.0%Min ^*data from raw suppliers

Dimethyl 2,2'-Bipyridine-6,6'-dicarboxylate >95.0%(GC) ^*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)C2=NC(=CC=C2)C(=O)OC

Technology Process of DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE

There total 8 articles about DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE 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: 95.0%

methanol (67-56-1) + 2,2'-bipyridine-6,6'-dicarboxylic acid (4479-74-7) → dimethyl 2,2'-bipyridine-6,6'-dicarboxylate (142593-07-5)

Guidance literature:

With sulfuric acid; for 16h; Reflux; Inert atmosphere;

DOI:10.1002/chem.201705283

Reference yield: 87.0%

methanol (67-56-1) + 2,2′-bipyridine-6,6′-dicarbonitrile (4411-83-0) → dimethyl 2,2'-bipyridine-6,6'-dicarboxylate (142593-07-5)

Guidance literature:

With sodium methylate; at 20 ℃;

DOI:10.1055/s-1999-2800

Reference yield: 75.0%

methanol (67-56-1) + 6,6'-dimethyl-2,2'-bipyridine (4411-80-7) → dimethyl 2,2'-bipyridine-6,6'-dicarboxylate (142593-07-5)

Guidance literature:

6,6'-dimethyl-2,2'-bipyridine; With chromium(VI) oxide; sulfuric acid; at 70 ℃; Cooling with ice;

methanol; at 70 ℃; for 24h;

DOI:10.1016/j.saa.2020.118898

upstream raw materials:

methanol

2,2′-bipyridine-6,6′-dicarbonitrile

[2,2']Bipyridinyl-6,6'-dicarboximidic acid dimethyl ester

2,2'-bipyridine-6,6'-dicarboxylic acid

Downstream raw materials:

6,6′-bis(hydroxymethyl)-2,2′-bipyridine

2,2'-bipyridine-6,6'-dicarbaldehyde

Refernces

• 1、 Heirtzler, Fenton R.. "Preparation of non-symmetrical 2,3-bis-(2,2'-oligopyridyl)pyrazines via 1,2-disubstituted ethanones". . p. 1203 - 1206. Retrieved 1999.
• 2、 Anwar, Muhammad U.,Al-Harrasi, Ahmed,Gavey, Emma L.,Pilkington, Melanie,Rawson, Jeremy M.,Thompson, Laurence K.. "A new nitrogen rich open chain diazine ligand system: Synthesis coordination chemistry and magneto-structural studies". . p. 2511 - 2521. Retrieved 2018.
• 3、 Forato, Florian,Belhboub, Anouar,Monot, Julien,Petit, Marc,Benoit, Roland,Sarou-Kanian, Vincent,Fayon, Franck,Jacquemin, Denis,Queffelec, Clémence,Bujoli, Bruno. "Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts". supporting information. p. 2457 - 2465. Retrieved 2018/02/06.