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

Base Information

• Chemical Name: 2,2'-bipyridine-6,6'-dicarbaldehyde
• CAS No.: 49669-26-3
• Molecular Formula: C₁₂H₈N₂O₂
• Molecular Weight: 212.208
• DSSTox Substance ID: DTXSID90407201
• Nikkaji Number: J2.041.330A
• Wikidata: Q82212443
• Mol file: 49669-26-3.mol

Synonyms:2,2'-bipyridine-6,6'-dicarbaldehyde

Chemical Property of 2,2'-bipyridine-6,6'-dicarbaldehyde

Chemical Property:

• Melting Point: 236-237 °C
• Boiling Point: 392.8±42.0 °C(Predicted)
• PKA: 2.83±0.10(Predicted)
• Density: 1.289±0.06 g/cm3(Predicted)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 212.058577502
• Heavy Atom Count: 16
• Complexity: 231

Purity/Quality:

98.5% ^*data from raw suppliers

6-(6-formylpyridin-2-yl)pyridine-2-carbaldehyde 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 2,2'-bipyridine-6,6'-dicarbaldehyde

There total 15 articles about 2,2'-bipyridine-6,6'-dicarbaldehyde 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: 100.0%

6,6′-bis(hydroxymethyl)-2,2′-bipyridine (74065-63-7) → 2,2'-bipyridine-6,6'-dicarbaldehyde (49669-26-3)

Guidance literature:

With SIBX; In ethyl acetate; Reflux; Inert atmosphere;

DOI:10.1002/chem.201705283

Reference yield: 77.0%

6,6'-di(1,3-dioxolan-2-yl)-2,2'-bipyridine (49669-32-1) → 2,2'-bipyridine-6,6'-dicarbaldehyde (49669-26-3)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/S0022-328X(97)00176-9

Reference yield: 70.0%

6,6'-Dibromo-2,2'-bipyridine (49669-22-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,2'-bipyridine-6,6'-dicarbaldehyde (49669-26-3)

Guidance literature:

6,6'-Dibromo-2,2'-bipyridine; With n-butyllithium; In tetrahydrofuran; at -90 ℃; for 0.75h;

N,N-dimethyl-formamide; In tetrahydrofuran; at -80 - -30 ℃; Further stages.;

DOI:10.1055/s-2006-944192

upstream raw materials:

6,6'-di(1,3-dioxolan-2-yl)-2,2'-bipyridine

6,6'-dimethyl-2,2'-bipyridine

6,6'-Dibromo-2,2'-bipyridine

N,N-dimethyl-formamide

Downstream raw materials:

6,6'-bis(aldimino)-2,2'-bipyridine (2,6-diisopropylanil)

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

6,6'-di(chloromethyl)-2,2'-bipyridine

Refernces

• 1、 Alzakhem, Nicola,Bischof, Caroline,Seitz, Michael. "Dependence of the photophysical properties on the number of 2,2′-bipyridine units in a series of luminescent europium and terbium cryptates". . p. 9343 - 9349. Retrieved 2012.
• 2、 Newkome, George R.,Onishi, Masayoshi,Puckett, Wallace E.,Deutsch, Walter A.. "Antitumor Agents. Synthesis of Novel cis-Palladium Complexes and Their Action on Supercoiled DNA". . p. 4551 - 4552. Retrieved 1980.
• 3、 Falk, H.,Suste, A.. "On the Chemistry of Pyrrole Pigments, XC: Pyridinologous Linear Tri- and Tetrapyrroles". . p. 881 - 892. Retrieved 1993.
• 4、 Ogawa, Ayumu,Oohora, Koji,Gu, Wenting,Hayashi, Takashi. "Electrochemical CO2 reduction by a cobalt bipyricorrole complex: Decrease of an overpotential value derived from monoanionic ligand character of the porphyrinoid species". . p. 493 - 496. Retrieved 2019.
• 5、 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". . p. 2457 - 2465. Retrieved 2018/02/06.