4,4'-Bis(chloromethyl)-2,2'-bipyridyl

• CAS: 138219-98-4
• Catalog Number: ACM138219984-2
• Category: Main Products
• Molecular Weight: 253.12
• Molecular Formula: C12H10Cl2N2
• Synonyms: 4-(chloromethyl)-2-[4-(chloromethyl)pyridin-2-yl]pyridine
• IUPAC Name: 4-(chloromethyl)-2-[4-(chloromethyl)pyridin-2-yl]pyridine
• Canonical SMILES: C1=CN=C(C=C1CCl)C2=NC=CC(=C2)CCl
• InChI: InChI=1S/C12H10Cl2N2/c13-7-9-1-3-15-11(5-9)12-6-10(8-14)2-4-16-12/h1-6H,7-8H2
• InChI Key: VZKSOWFFOHQARA-UHFFFAOYSA-N
• Appearance: Powder or crystal
• Complexity: 191
• Covalently-Bonded Unit Count: 1
• Exact Mass: 252.022104g/mol
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Heavy Atom Count: 16
• Monoisotopic Mass: 252.022104g/mol
• Rotatable Bond Count: 3
• XLogP3: 2.3

Case Study

4,4'-Bis(Chloromethyl)-2,2'-Bipyridine for the Synthesis of Functionalized 4,4'-Disubstituted-2,2'-Bipyridines

Klein C, et al. Tetrahedron Letters, 2010, 51(47), 6161-6165.

A synthetic route to expand the π system on 4,4'-disubstituted-2,2'-bipyridines is reported to develop a series of novel functionalized 2,2'-bipyridine ligands, which can be used in dye-sensitized solar cell (DSC) applications. In the synthetic route, 4,4'-bis(chloromethyl)-2,2'-bipyridine (7) is the intermediate compound for the synthesis of compound 8 [4,4'-Bis(diethylmethylphosphonate)-2,2'-bipyridine]. Subsequently, compound 8 can be used to synthesize a series of functionalized bipyridines via the Horner-Emmons-Wadsworth reaction.
Synthetic procedure starting from 4,4'-bis(chloromethyl)-2,2'-bipyridine
· A solution of 4,4'-bis(chloromethyl)-2,2'-bipyridine (7) (2.6 g, 10.3 mmol) in triethylphosphite (50 ml) was heated to 160 °C overnight in a nitrogen atmosphere. After the excess P(OEt)3 was removed by evaporation, a brown oil remained. This crude product was then purified through column chromatography using SiO2 and a solvent mixture of EtOAc/MeOH in an 80:20 ratio, resulting in 4 g (85%) of compound 8 as a white solid.
· For the general procedure in synthesizing functionalized bipyridines, a solution containing 8 (1 g, 2.2 mmol) and the relevant benzaldehyde 21a-f (2.5 equivalents) in anhydrous DMF (50 ml) received solid t-BuOK (4 equivalents). A substantial precipitate formed within a few minutes. The mixture was stirred overnight at room temperature under nitrogen. Following the evaporation of DMF, 150 ml of MeOH was added to the mixture. It was sonicated for 2 minutes and then left to stand in the refrigerator for 1 hour before being filtered. The resulting solid was washed with small increments of cold MeOH and allowed to air dry, yielding pure compounds 22a-f.

4,4'-Bis(Chloromethyl)-2,2'-Bipyridine Used in the Synthesis of Amphiphilic Ruthenium (II) Complexes Containing 2,2'-Bipyridine Ligands

Kirilov P, et al. Applied organometallic chemistry, 2006, 20(2), 125-129.

Ruthenium (II) complexes of 2,2'-bipyridine ligands and their derivatives have attracted attention because of their photoinduced electron and energy transfer properties. This work introduces the synthesis of a series of metal-free 4,4'-dialkylaminomethyl-2,2'-bipyridine ligands and the corresponding ruthenium (II) complexes.
Synthesis of ligands and ruthenium (II) complexes
· The ligands 4,4'-dialkylaminomethyl-2,2'-bipyridine (3a, 3b, and 3c) were synthesized by refluxing dialkylamine with 4,4'-bis(chloromethyl)-2,2'-bipyridine in acetonitrile (CH3CN) in the presence of potassium carbonate (K2CO3). They were then purified using a silica column with a solvent mixture of ethyl acetate and hexane in a 1:1 ratio.
· Subsequently, three distinct types of ruthenium complexes featuring alkylaminomethyl-substituted bipyridyl ligands were created, specifically the homoleptic complexes [Ru(L)₃]²⁺ (PF^6-)₂ (4a with L = 3a; 4b with L = 3b; and 4c with L = 3c). The synthesis of these complexes involved a 1:3 molar ratio of the relevant ruthenium(III) chloride precursor and the 4,4'-dialkylaminomethyl-2,2'-bipyridine ligand in absolute ethanol, refluxed under an argon atmosphere for approximately six hours. During the reaction, the violet solution transitioned to a more vivid red-orange, indicating the formation of the complexes.

Custom Q&A

What is the molecular formula of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl?

The molecular formula is C12H10Cl2N2.

When was the structure of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl created and last modified?

The structure was created on 2006-10-25 and last modified on 2023-12-30.

What is the InChIKey of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl?

The InChIKey is VZKSOWFFOHQARA-UHFFFAOYSA-N.

How many hydrogen bond acceptors does 4,4'-Bis(chloromethyl)-2,2'-bipyridyl have?

It has 2 hydrogen bond acceptors.

What is the topological polar surface area of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl?

The topological polar surface area is 25.8 Ų.

What is the XLogP3-AA value of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl?

The XLogP3-AA value is 2.3.

What is the exact mass of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl?

The exact mass is 252.0221037 g/mol.

How many rotatable bond counts does 4,4'-Bis(chloromethyl)-2,2'-bipyridyl have?

It has 3 rotatable bond counts.

Is 4,4'-Bis(chloromethyl)-2,2'-bipyridyl considered a canonicalized compound?

Yes, it is considered a canonicalized compound.

What is the complexity value of 4,4'-Bis(chloromethyl)-2,2'-bipyridyl?

The complexity value is 191.