Dimethyl [3,3'-bipyridine]-5,5'-dicarboxylate

Base Information

• Chemical Name: Dimethyl [3,3'-bipyridine]-5,5'-dicarboxylate
• CAS No.: 128612-43-1
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.26
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70428419
• Nikkaji Number: J258.419K
• Mol file: 128612-43-1.mol

Synonyms:128612-43-1;Dimethyl [3,3'-bipyridine]-5,5'-dicarboxylate;Dimethyl 3,3'-Bipyridine-5,5'-dicarboxylate;methyl 5-(5-methoxycarbonylpyridin-3-yl)pyridine-3-carboxylate;DIMETHYL 3,3/'-BIPYRIDINE-5,5/'-DICARBOXYLATE;[3,3']bipyridinyl-5,5'-dicarboxylic acid dimethyl ester;Dimethyl 5,5'-bipyridine-3,3'-dicarboxylate;Dimethyl[3,3'-bipyridine]-5,5'-dicarboxylate;SCHEMBL3715051;DTXSID70428419;MFCD07363810;AKOS015854382;BS-20618;CS-0089802;A889003;Dimethyl [3,3/'-bipyridine]-5,5/'-dicarboxylate;J-005614;Methyl 5-[5-(methoxycarbonyl)pyridin-3-yl]nicotinate;3,3'-Bipyridine-5,5'-dicarboxylic acid dimethyl ester;[3,3'-Bipyridine]-5,5'-dicarboxylicacid,5,5'-dimethyl ester

Chemical Property of Dimethyl [3,3'-bipyridine]-5,5'-dicarboxylate

Chemical Property:

• Melting Point: 226-230 °C
• Boiling Point: 443.1 °C at 760 mmHg
• Flash Point: 221.8 °C
• PSA: 78.38000
• Density: 1.254 g/cm³
• LogP: 1.71680
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.1
• 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:

99% ^*data from raw suppliers

Dimethyl3,3''-bipyridine-5,5''-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN=CC(=C1)C2=CC(=CN=C2)C(=O)OC
• Uses: Dimethyl 3,3''-bipyridine-5,5''-dicarboxylate

Technology Process of Dimethyl [3,3'-bipyridine]-5,5'-dicarboxylate

There total 4 articles about Dimethyl [3,3'-bipyridine]-5,5'-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: 73.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) → 5,5'-Bis(methoxycarbonyl)-3,3'-bipyridine (128612-43-1)

Guidance literature:

dibromobis(triphenylphosphine)nickel(II); tetraethylammonium iodide; zinc; In tetrahydrofuran; at 50 ℃; for 20h;

DOI:10.1246/bcsj.63.80

Reference yield: 63.5%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarboxylic acid methyl ester (1025718-91-5) → 5,5'-Bis(methoxycarbonyl)-3,3'-bipyridine (128612-43-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; for 72h; Reflux; Inert atmosphere;

DOI:10.1021/acs.inorgchem.1c02363

Reference yield: 50.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + 6-bromo-2-methoxypyridine (40473-07-2) → 5,5'-Bis(methoxycarbonyl)-3,3'-bipyridine (128612-43-1) + 6-methoxy-[2,3']bipyridinyl-5'-carboxylic acid methyl ester (321535-19-7)

Guidance literature:

With bis(tri-n-butyltin); trans benzyl(chloro)bis(triphenylphosphine)palladium(II); In N,N-dimethyl-formamide; at 130 ℃; for 1h;

DOI:10.1021/ol0067538

upstream raw materials:

5-bromo-3-pyridine carboxylic acid methyl ester

6-bromo-2-methoxypyridine

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarboxylic acid methyl ester

Refernces

• 1、 Dibenedetto, Tarah A.,Kang, Kai,Loud, Nathan L.,Weix, Daniel J.. "A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates". supporting information. p. 21484 - 21491. Retrieved 2022/01/03.
• 2、 Iyoda,Otsuka,Sato,Nisato,Oda. "Homocoupling of aryl halides using Nickel(II) complex and zinc in the presence of Et4NI. An efficient method for the synthesis of biaryls and bipyridines". . p. 80 - 87. Retrieved 2007/10/02.