4,4'-Bis(bromomethyl)-2,2'-bipyridine

• CAS: 134457-14-0
• Catalog Number: ACM134457140-2
• Category: Main Products
• Molecular Weight: 342.03
• Molecular Formula: C12H10Br2N2
• Synonyms: 4-(Bromomethyl)-2-[4-(bromomethyl)pyridin-2-yl]pyridine
• IUPAC Name: 4-(bromomethyl)-2-[4-(bromomethyl)pyridin-2-yl]pyridine
• InChI: XCMRHOMYGPXALN-UHFFFAOYSA-N
• InChI Key: InChI=1S/C12H10Br2N2/c13-7-9-1-3-15-11(5-9)12-6-10(8-14)2-4-16-12/h1-6H,7-8H2
• Boiling Point: 135-137 °C
• Melting Point: 135-137 °C
• Appearance: White solid
• Isomeric SMILES: C1=CN=C(C=C1CBr)C2=NC=CC(=C2)CBr

Case Study

4,4'-Bis(Bromomethyl)-2,2'-Bipyridine for the Synthesis of Dendritic Bipyridine Ligands

Jahier, Claire, et al. Journal of Organometallic Chemistry, 2009, 694(5), 637-642.

A series of bipyridine ligands containing 6- and 18-arm dendritic polyallyl and polyferrocenyl groups were synthesized by coupling 4,4'-bis(bromomethyl)-2,2'-bipyridine with AB3 and AB9 dendrimers.
General procedure for the synthesis of dendritic bipyridine ligands
· One equivalent of 4,4'-bis(bromomethyl)-2,2'-bipyridine (1) was reacted with two equivalents of dendron in the presence of three equivalents of K2CO3 in acetonitrile (CH3CN). The resulting mixture was stirred at reflux for 24 hours. After the solvent was removed under vacuum, the product was extracted using diethyl ether (Et2O) and subsequently dried over sodium sulfate (Na2SO4). The solvent was then evaporated, and the resulting product was purified through chromatography (silica gel, using a pentane/diethyl ether ratio of 8:2, followed by diethyl ether). The dendritic 6-allyl bipyridine ligand (4) was obtained as a white solid with an 85% yield. The dendritic 18-allyl bipyridine ligand (5) was acquired as a white solid with a 90% yield.
· In a similar manner, the dendritic 18-ferrocenyl bipyridine ligand (7) was obtained as an orange solid with an 89% yield, utilizing a solvent mixture of acetonitrile and tetrahydrofuran (THF) in a 1:1 volume ratio, instead of just acetonitrile.

4,4'-Bis(Bromomethyl)-2,2.-Bipyridine for the Synthesis of Trinuclear Ru(II) Complexes

Cheng, Feixiang, et al. Journal of Coordination Chemistry, 2015, 68(4), 704-716.

Three heterotopic ligands L1-3 were prepared by reacting 4,4'-bis(bromomethyl)-2,2'-bipyridine with different compounds in DMF, respectively. Subsequently, the Ru(II) complexes [{Ru(bpy)2}3(μ3-L1-3)](PF6)6 (bpy = 2,2'-bipyridine) were prepared by refluxing Ru(bpy)2Cl2·2H2O and these ligands in 2-methoxyethanol.
Synthesis procedure of ligands L1-3
· To synthesize 4,4'-Bis[(4,5-diazafluoren-9-ylimino)methyl]-2,2'-bipyridine (L1), combine 4,4'-bis(bromomethyl)-2,2'-bipyridine (213 mg, 0.63 mmol), 4,5-diazafluoren-9-oxime (383 mg, 1.94 mmol), and potassium carbonate (337 mg, 2.44 mmol) in 30 mL of dimethylformamide (DMF). Heat the mixture to 90 °C under a nitrogen atmosphere for 48 hours. Upon completion, allow the solution to cool to room temperature, then add it to 300 mL of water. Collect the resulting white precipitate by filtration. The crude product is purified via silica gel chromatography to obtain the desired product as a white solid.
· 4,4'-Bis[2-(4,5-diazafluoren-9-ylimino)phenoxymethyl]-2,2'-bipyridine (L2) is synthesized using a procedure analogous to that of L1, substituting 4,5-diazafluoren-9-oxime with 9-(2-hydroxy)phenylimino-4,5-diazafluorene (481 mg, 1.76 mmol) in conjunction with 4,4'-bis(bromomethyl)-2,2'-bipyridine (187 mg, 0.55 mmol).
· The synthesis of 4,4'-Bis[4-(4,5-diazafluoren-9-ylimino)phenoxymethyl]-2,2'-bipyridine (L3) follows the same methodology as L1, with the substitution of 4,5-diazafluoren-9-oxime for 9-(4-hydroxy)phenylimino-4,5-diazafluorene (438 mg, 1.60 mmol) and the reaction using 4,4'-bis(bromomethyl)-2,2'-bipyridine (162 mg, 0.48 mmol).

Custom Q&A

What is the molecular weight of 4,4-Bis(bromomethyl)-2,2-bipyridine?

The molecular weight is 342.03 g/mol.

When was this compound created and when was it last modified?

It was created on October 26, 2006, and last modified on December 30, 2023.

What is the IUPAC name of this compound?

The IUPAC name is 4-(bromomethyl)-2-[4-(bromomethyl)pyridin-2-yl]pyridine.

How many hydrogen bond acceptor counts does this compound have?

It has 2 hydrogen bond acceptor counts.

What is the Canonical SMILES representation of this compound?

The Canonical SMILES representation is C1=CN=C(C=C1CBr)C2=NC=CC(=C2)CBr.

What is the InChIKey of this compound?

The InChIKey is XCMRHOMYGPXALN-UHFFFAOYSA-N.

How many rotatable bond counts does this compound have?

It has 3 rotatable bond counts.

What is the exact mass of this compound?

The exact mass is 341.91902 g/mol.

Does this compound have any defined atom stereocenters?

No, it does not have any defined atom stereocenters.

Is the compound canonicalized?

Yes, the compound is canonicalized.