74309-54-9

Basic information

• Product Name: 2-[1-(2-methylphenyl)]ethenylpyridine
• Synonyms: 2-[1-(2-methylphenyl)]ethenylpyridine
• CAS NO: 74309-54-9
• Molecular Formula: C₁₄H₁₃N
• Molecular Weight: 195.26
• Mol File: 74309-54-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 302.9 °C at 760 mmHg
• Flash Point: 126.3 °C
• Appearance: /
• Density: 1.02 g/cm³
• Vapor Pressure: 0.00173mmHg at 25°C
• Refractive Index: 1.573
• PKA: 3.96±0.10(Predicted)
• CAS DataBase Reference: 2-[1-(2-methylphenyl)]ethenylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[1-(2-methylphenyl)]ethenylpyridine(74309-54-9)
• EPA Substance Registry System: 2-[1-(2-methylphenyl)]ethenylpyridine(74309-54-9)

Safety Data

• Hazardous Substances Data: 74309-54-9(Hazardous Substances Data)

Usage

General Description

2-[1-(2-methylphenyl)]ethenylpyridine is a chemical compound also known as 2-methylphenylethynylpyridine. It is a derivative of pyridine with a methylphenyl and ethynyl group attached to it. 2-[1-(2-methylphenyl)]ethenylpyridine is frequently used in organic synthesis as a building block for various functional materials and pharmaceuticals. It is also known for its high efficiency as a blue light emitter in organic light-emitting diodes (OLEDs) due to its strong electron-accepting nature and good fluorescent properties. Additionally, it has been studied for its potential antiproliferative and neuroprotective activities, showing promise for application in medicinal chemistry and drug development. Overall, 2-[1-(2-methylphenyl)]ethenylpyridine is a versatile and valuable chemical compound with a wide range of potential applications in various fields.

InChI:InChI=1/C14H13N/c1-11-7-3-4-8-13(11)12(2)14-9-5-6-10-15-14/h3-10H,2H2,1H3

Upstream product

• 54523-78-3 (pyridin-2-yl)(o-tolyl)methanone 
• 36995-45-6 2-[(2-methylphenyl)methyl]pyridine 
• 127-19-5 N,N-dimethyl acetamide 
• 1122-62-9 2-acetylpyridine 
• 59742-91-5 2-acetylpyridine hydrazone 
• 95-46-5 2-methylphenyl bromide 
• 54856-82-5 3-methyl-[1,2,3]triazolo[1,5-a]pyridine 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 98-98-6 2-Picolinic acid 

Relevant articles and documents

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts

Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.

Palladium-Catalyzed Divergent Arylation with Triazolopyridines: One-Pot Synthesis of 6-Aryl-2-α-styrylpyridines

We have developed a new strategy for palladium-catalyzed arylation reactions with triazolopyridines, wherein two different chemical transformations (C-3 vs. C-7) are observed by differentiating the substrates using different bases. The reactive palladium carbenoids were directly generated from triazolopyridines and underwent denitrogenative arylations with aryl bromides. Intriguingly, when potassium carbonate was replaced with potassium tert-butoxide, direct C-H arylation occurred at the most acidic position (C-7). Moreover, two different catalytic arylation events were successfully performed in a one-pot sequence, providing a convenient access to 6-aryl-2-α-styrylpyridines.

Copper-catalyzed α-methylenation of benzylpyridines using dimethylacetamide as one-carbon source

The direct α-methylenation of benzylpyridines was achieved using N,N-dimethylacetamide (DMA) as a one-carbon source under copper catalysis. An intermediary species was detected at an early stage, and a possible mechanism was proposed. Additionally, α-oxygenation and dimerization of benzylpyridines could also be performed efficiently.