6,6'-Dimethyl-2,2'-bipyridine

Base Information

• Chemical Name: 6,6'-Dimethyl-2,2'-bipyridine
• CAS No.: 4411-80-7
• Molecular Formula: C12H12N2
• Molecular Weight: 184.241
• Hs Code.: 29333990
• European Community (EC) Number: 224-566-5
• NSC Number: 4705
• UNII: AF3HZ0ZAN4
• DSSTox Substance ID: DTXSID30196041
• Nikkaji Number: J23.946A
• Wikidata: Q72469922
• ChEMBL ID: CHEMBL2205806
• Mol file: 4411-80-7.mol

Synonyms:6,6'-Dimethyl-2,2'-bipyridine;4411-80-7;6,6'-Dimethyl-2,2'-bipyridyl;6,6'-Bi-2-picoline;6,6'-Dimethyl-2,2'-dipyridyl;2,2'-BIPYRIDINE, 6,6'-DIMETHYL-;2-methyl-6-(6-methylpyridin-2-yl)pyridine;NSC 4705;EINECS 224-566-5;AF3HZ0ZAN4;BRN 0128972;CHEMBL2205806;6,6'-dimethyl-2,2'-dipyridine;NSC-4705;MFCD00059776;6,6-Di-2-Picolyl;NSC4705;Bipicoline;98%;6,6'-Di-2-picolyl;UNII-AF3HZ0ZAN4;SCHEMBL196966;YSSJ00798;DTXSID30196041;BCP30986;BDBM50401355;AKOS000268334;AC-7735;CS-W004545;6,6'-Dimethyl-2,2'-dipyridyl, 98%;AS-20071;LS-44631;SY052412;2-methyl-6-(6-methyl-2-pyridinyl)pyridine;AM20051181;B0842;FT-0692834;EN300-1697612;A826492;W-200553;6,6 inverted exclamation mark -Dimethyl-2,2 inverted exclamation mark -bipyridyl

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

Chemical Property:

• Melting Point: 93-95 °C(lit.)
• Boiling Point: 278.6 °C at 760 mmHg
• PKA: 5.20±0.22(Predicted)
• Flash Point: 104.9 °C
• PSA: 25.78000
• Density: 1.061 g/cm³
• LogP: 2.76040
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.100048391
• Heavy Atom Count: 14
• Complexity: 161

Purity/Quality:

6,6''-Dimethyl-2,2’-bipyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=CC=C1)C2=CC=CC(=N2)C
• Uses: 6,6′-dimethyl-2,2′-bipyridyl (6,6′-Dimethyl-2,2′-bipyridine)may be used in the synthesis of novel oligobipyridine ligands.

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

There total 48 articles about 6,6'-Dimethyl-2,2'-bipyridine 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: 99.0%

2-bromo-6-methylpyridine (5315-25-3) → 6,6'-dimethyl-2,2'-bipyridine (4411-80-7)

Guidance literature:

With Ni(acetylacetate)2; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene; In toluene; at 80 ℃; for 18h;

DOI:10.1002/anie.201507902

Reference yield: 93.1%

2-bromo-6-methylpyridine (5315-25-3) → α-picoline (109-06-8) + 6,6'-dimethyl-2,2'-bipyridine (4411-80-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 2-pentanol; at 100 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jo100089d

Reference yield: 78.0%

2-bromo-6-methylpyridine (5315-25-3) + 2,6-dichloropyridine (2402-78-0) → 6,6'-dimethyl-2,2'-bipyridine (4411-80-7) + 6,6-dimethyl-2,2':6',2-terpyridine (33777-92-3)

Guidance literature:

With bis(bipyridine)nickel(II) bromide; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 8h; Electrochemical reaction; Inert atmosphere;

DOI:10.1016/j.tet.2012.01.017

upstream raw materials:

α-picoline

2-bromo-6-methylpyridine

2-Ethanesulfinyl-6-methyl-pyridine

benzyltri(2-(6-methylpyridyl))phosphonium bromide

Downstream raw materials:

6-(bromomethyl)-6'-methyl-2,2'-bipyridine

6,6'-bis-(bromomethyl)-2,2'-bipyridine

6-Dichloromethyl-6'-methyl-[2,2']bipyridinyl

6'-Chloromethyl-6-dichloromethyl-[2,2']bipyridinyl

Refernces

• 1、 Pordel, Shabnam,Schrage, Briana R.,White, Jessica K.,Ziegler, Christopher J.. "Impact of steric bulk on photoinduced ligand exchange reactions in Mn(I) photoCORMs". . . Retrieved 2020.
• 2、 Yazdani, Sima,Silva, Braden E.,Cao, Thomas C.,Rheingold, Arnold L.,Grotjahn, Douglas B.. "X-ray crystallography and electrochemistry reveal electronic and steric effects of phosphine and phosphite ligands in complexes RuII(κ4-bda)(PR3)2 and RuII(κ3-bda)(PR3)3 (bda?=?2,2′-bipyridine-6,6′-dicarboxylato)". . p. 63 - 70. Retrieved 2019.
• 3、 Shaul, Mazi,Cohen, Yoram. "Novel phenanthroline-containing trinuclear double-stranded helicates: Self-recognition between helicates with phenanthroline and bipyridine binding sites". . p. 9358 - 9364. Retrieved 1999.
• 4、 Alyapyshev,Babain,Borisova,Eliseev,Kirsanov,Kostin,Legin,Reshetova,Smirnova. "2,2′-Dipyridyl-6,6′-dicarboxylic acid diamides: Synthesis, complexation and extraction properties". . p. 1998 - 2005. Retrieved 2010.
• 5、 Cassol,Demnitz,Navarro,Neves. "Two convenient and high-yielding preparations of 6,6'-dimethyl-2,2'-bipyridine by homocoupling of 6-bromopicoline". . p. 8203 - 8206. Retrieved 2000.
• 6、 Beynek, Nesrin,Tan, Nurcihan,Beynek, Hayrettin. "Template synthesis, characterization, and antimicrobial activity of a new lead (II) Schiff base complex". . p. 145 - 150. Retrieved 2015.
• 7、 Beynek,Tan,Beynek. "Template synthesis and spectral characterization of new Lead(II)-Schiff base macrocyclic complexes incorporating phenanthroline and/or bipyridine units". . p. 4141 - 4144. Retrieved 2015.
• 8、 Santoro, Antonio,Holub, Jan,Fik-Jaskó?ka, Marta A.,Vantomme, Ghislaine,Lehn, Jean-Marie. "Dynamic Helicates Self-Assembly from Homo- and Heterotopic Dynamic Covalent Ligand Strands". supporting information. p. 15664 - 15671. Retrieved 2020/10/21.