6630-11-1

Usage

Uses

Used in Coordination Chemistry:
Bis(6-methyl-2-pyridyl) diketone is used as a bidentate ligand for forming stable complexes with metal ions. Its ability to chelate metal ions makes it a valuable reagent in the synthesis of metal-organic frameworks and coordination polymers.
Used in Organometallic Chemistry:
MMDK is used as a ligand in organometallic chemistry to stabilize metal complexes, which can be employed in various catalytic processes.
Used in Catalysis:
Bis(6-methyl-2-pyridyl) diketone is used as a catalyst or catalyst precursor in various chemical reactions, owing to its ability to form stable complexes with metal ions and its potential to modulate the reactivity and selectivity of the catalysts.
Used in Materials Science:
MMDK is used in the development of new materials, such as metal-organic frameworks and coordination polymers, which have potential applications in gas storage, separation, and sensing.
Used in Medicinal Chemistry:
Bis(6-methyl-2-pyridyl) diketone is used as a building block or a ligand in the design and synthesis of new pharmaceutical compounds, taking advantage of its ability to form stable complexes with metal ions and its potential to modulate biological activity.

InChI:InChI=1/C14H12N2O2/c1-9-5-3-7-11(15-9)13(17)14(18)12-8-4-6-10(2)16-12/h3-8H,1-2H3

Upstream product

• 7252-50-8 2-hydroxy-[1,2-bis(6-methylpyridin-2-yl)]ethan-1-one 
• 1121-60-4 pyridine-2-carbaldehyde 
• 1122-71-0 2-(Hydroxymethyl)-6-methylpyridine 
• 148168-75-6 6,6'-dimethyl-2,2'-pyridoin 

Downstream Products

• 1122-72-1 6-methyl-2-pyridinecarboxaldehyde 
• 99765-49-8 bis(6-methylpyridin-2-yl)methanone 
• 7252-50-8 2-hydroxy-[1,2-bis(6-methylpyridin-2-yl)]ethan-1-one 

Relevant academic research and scientific papers

2,2′-Pyridoin derivatives protect HL-60 cells against oxidative stress

Focusing on 2,2′-pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) and its synthetic derivatives as the lead compound of the potent antioxidative enediol, their protective effect against oxidative stress was evaluated on the HL-60 cell system. 2,2′-Pyridoins showed no remarkable cytotoxic effect on HL-60 cells. The derivatives 1, 2, 3, 5, and 6 inhibited H2O2-induced cell death and intracellular oxidative stress more significantly than ascorbic acid. Since 2,2′-pyridoins are oxidized to the diketones, 2,2′-pyridils, in a protic solvent, the antioxidant activity of 2,2′-pyridils was also investigated. 2,2′-Pyridils showed antioxidant activity in the cell; however, the activity was lower than that of 2,2′-pyridoins. These results suggested that 2,2′-pyrdoin derivatives can be good cytoprotective agents against oxidative stress.

Synthesis, characterisation and crystal structure of a co-crystal of two components: 1,2-bis(6-methylpyridin-2-yl)ethane-1,2-dione and 1-(pyridin-2-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione

A condensation reaction of an equimolar ratio of 2-pyridinecarboxaldehyde and (6-methylpyridin-2-yl)methanol without a catalyst in a solvent-free reaction at 140°C was expected to yield 2-hydroxy-[1,2-bis(6-methylpyridin-2-yl)] ethan-1-one. FT-IR spectroscopy of the yellow-brown solid reaction product indicated the presence of a -CO-COH- group. The solid compound was treated with cyclohexane and green crystals were produced. The crystals were characterised by FT-IR, 1H NMR, El mass spectrometry and single-crystal X-ray diffraction. The molecular and crystal structure determined by single-crystal X-ray diffraction resolved one crystal showing two molecular components [C 13H10N2O2 and C14H 12N2O2] at a ratio of 60.4:39.6 [C 13.40H10.79N2O2]. Both compounds co-crystallise in the triclinic space group P-1, with a = 7.859(5), b = 8.021(14), c = 9.060(5) A, α = 101.36(2)°, β= 90.06(3)°, γ = 90.92(3)°, V = 559.8(5) A3, Z= 2. The compounds were 1,2-bis(6-methylpyridin-2-yl)ethane-1,2-dione and 1-(pyridin-2-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione. These results are important because they confirm that condensation in a solvent- and catalyst-free reaction yielded precursors that were converted into α-diketone compounds by the action of solvent and oxygen.