345911-44-6

Basic information

• Product Name: (4-Ethynylphenyl)-4-pyridinylmethanone
• Synonyms: 4-(4-Ethynylbenzoyl)pyridine
• CAS NO: 345911-44-6
• Molecular Formula: C₁₄H₉NO
• Molecular Weight: 0
• Mol File: 345911-44-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Refractive Index: 1.619
• CAS DataBase Reference: (4-Ethynylphenyl)-4-pyridinylmethanone(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Ethynylphenyl)-4-pyridinylmethanone(345911-44-6)
• EPA Substance Registry System: (4-Ethynylphenyl)-4-pyridinylmethanone(345911-44-6)

Safety Data

• Hazardous Substances Data: 345911-44-6(Hazardous Substances Data)

Usage

General Description

(4-Ethynylphenyl)-4-pyridinylmethanone, also known as EP-4PM, is a chemical compound that belongs to the class of aromatic ketones. It has a molecular formula of C15H9NO and a molecular weight of 219.24 g/mol. EP-4PM is a yellow solid with a melting point of 200-203°C. (4-Ethynylphenyl)-4-pyridinylmethanone is often used in the pharmaceutical industry as a building block for the synthesis of various biologically active molecules, such as potential anti-inflammatory and anti-cancer agents. Its unique structure and reactivity make it a valuable tool for organic synthesis and medicinal chemistry research. However, care should be taken when handling EP-4PM, as it may pose health risks if not properly handled and used in a controlled environment.

InChI:InChI=1/C14H9NO/c1-2-11-3-5-12(6-4-11)14(16)13-7-9-15-10-8-13/h1,3-10H

Upstream product

• 14548-49-3 (4-bromo-phenyl)-pyridin-4-yl-methanone 
• 1066-54-2 trimethylsilylacetylene 
• 14254-57-0 4-(chlorocarbonyl)pyridine 
• 55-22-1 pyridine-4-carboxylic acid 
• 345911-43-5 4-(4-[(Trimethylsilyl)ethynyl]benzoyl)pyridine 

Relevant articles and documents

Tuning the redox chemistry of 4-benzoyl-N-methylpyridinium cations through para substitution. Hammett linear free energy relationships and the relative aptitude of the two-electron reduced forms for H-bonding

In anhydrous CH3CN a series of nine 4-(4-substituted-benzoyl)-N-methylpyridinium cations (substituent: -OCH3, -CH3, -H, -SCH3, -Br, -C≡CH, -CHO, -NO2, and -+S(CH3)2) demonstrate two chemically reversible, well-separated one-electron (1-e) reductions in the same potential range as other main stream redox catalysts such as quinones and viologens. Hammett linear free energy plots yield excellent correlation between the E1/2 values of both waves and the substituent constants σp-X. The reaction constants for the two 1-e reductions are ρ1 = 2.60 and ρ2 = 3.31. The lower ρ1 value is associated with neutralization of the pyridinium ring, and the higher ρ2 value with the negative charge developing during the 2nd-e reduction. Structure-function correlations point to a purely inductive role for substitution in both 1-e reductions. The case of the 4-(4-nitrobenzoyl)-N-methylpyridinium cation is particularly noteworthy, because the 4-nitrobenzoyl moiety undergoes reduction before the 2nd reduction of the 4-benzoyl-N-methylpyridinium system. Correlation of the third wave of this compound with the 2nd-e reduction of the others yields σp-NO2- = -0.97 ± 0.02, thus placing the -NO2- group among the strongest electron donors. Solvent deuterium isotope effects and maps of the electrostatic potential (via PM3 calculations) as a function of substitution support that 2-e reduced forms develop H-bonding with proton donors (e.g., CH3-OH) via the O-atom. The average number of CH3OH molecules entering the H-bonding association increases with e-donating substituents. H-bonding shifts the 2nd reduction wave closer to the first one. This has important practical implications, because it increases the equilibrium concentration of the 2-e reduced form from disproportionation of the 1-e reduced form.