72076-59-6

Basic information

• Product Name: Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)-
• CAS NO: 72076-59-6
• Molecular Formula: C14H13NO
• Molecular Weight: 211.263
• Mol File: 72076-59-6.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)-(72076-59-6)
• EPA Substance Registry System: Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)-(72076-59-6)

Safety Data

• Hazardous Substances Data: 72076-59-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)-, is employed as a key intermediate in the synthesis of various pharmaceutical compounds. Its presence of both aromatic and heterocyclic groups allows for the development of new drugs with diverse therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)- serves as a versatile building block for the creation of more complex organic molecules. Its reactivity can be harnessed to form a wide range of products, including other ketones, alcohols, and amines, which are essential in various chemical industries.
Used in Chemical Production:
Due to its unique chemical properties, Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)-, may also have various industrial applications. It could be used in the production of specialty chemicals, dyes, or as a component in the formulation of advanced materials.
Used in Research and Development:
In academic and industrial research settings, Ethanone, 1-(4-methylphenyl)-2-(2-pyridinyl)- is valuable for studying reaction mechanisms and exploring new synthetic routes. Its ability to participate in a variety of chemical reactions makes it an important tool for advancing the field of organic chemistry.

Upstream product

• 1749-29-7 2-pyridylmethyllithium 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 17881-80-0 (2-picolyl)trimethylsilane 
• 104-85-8 para-methylbenzonitrile 
• 109-06-8 α-picoline 
• 74115-44-9 (Z)-2-[2]pyridyl-1-p-tolyl-vinyl alcohol 

Downstream Products

• 92360-03-7 (C₅H₄NCH₂COC₆H₄CH₃Co(NCS)2) 
• 92360-20-8 C₅H₄NCH₂COC₆H₄CH₃Ni(NCS)2 
• 92360-23-1 (C₅H₄NCH₂COC₆H₄CH₃)2Ni(NCS)2 

Relevant articles and documents

Tautomer-selective derivatives of enolate, ketone and enaminone by addition reaction of picolyl-type anions with nitriles

We describe an efficient for the synthesis of compounds of tautomeric β-pyridyl/quinolyl-enol, -ketone, -enaminone, which were finally characterized by standard methods like NMR, IR or SCXRD. The addition reaction of lithiated intermediates of picoline, 2-ethylpyridine and 2-methylquinoline, respectively, with nitriles followed by acid hydrolysis afforded the corresponding tautomeric compounds of enol, ketone and emaminone. Interestingly, treatment of 2-methylpyridine or 2-ethylpyridine with nitriles, respectively, yielded mostly β-pyridyl ketone and enol tautomers without enaminones, while 2-methylquinoline with nitriles gave β-quinolyl ketone and enaminone tautomers without enols. The reaction of 2-benzylpyridine with nitriles was not available under the same conditions.

Substituent and temperature controlled tautomerism of 2-phenacyl-pyridine: The hydrogen bond as a configurational lock of (Z)-2-(2-hydroxy-2-phenylvinyl)pyridine

2-Phenacylpyridines substituted in the benzene ring are in equilibrium with (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines when dissolved in chloroform. The substituent affects significantly the tautomeric equilibrium [the amount of the enolimine form stabilized by the intramolecular hydrogen bond is 1 and 92% for R = p-N(CH2)4 and p-NO2, respectively]. The negative logarithm of the tautomeric equilibrium constant, KT, is linearly dependent on the Hammett σ substituent constants. The dependence of KT vs. temperature is exponential in character: the more electron-withdrawing is the substituent, the more distinct is the influence of temperature. Unexpectedly, the tautomer present in the crystalline state is not the same for all compounds studied (it is the ketimine one for those carrying strong electron-donor groups). Among the different ab initio methods used to calculate the enthalpy of the proton transfer in chloroform solution, MP2/6-31G** gives the best results.

Chiroptical, Structural and Catalytic Properties of S-α-Methyl-benzylamines and their Rh(I) and Cu(I) Complexes

S-α-Methyl-benzylamines 15-21 and their Rh(I) complexes 22-28 are prepared and their chiroptical and conformational properties are studied.Free ligands are present as enamines in the solution and in the solid state, but are bound to Rh(I) in the imine form.The CD spectra confirm that complexation of 15-21 induces both structural change and strong conformational perturbations.The molecular structures in the crystal are reported for the chiral 1,5-bisnitrogen ligand 18, and its Rh perchlorate complex 25.The absolute conformation of the chromophore in 18 inverts on binding to Rh(I) in 25.The value of the torsional angle about C10-C9-C16-C21 bond (- 69.7 deg) in 18, which defines the twisted stilbene-like chromophore, turns for 25 into 75.0 deg.Chiral (S)-(-)-methylbenzyl subunit in 18 has a C1-N1-C9-C10 torsional angle of 175.2 deg, whereas on binding to Rh(I) in 25 this angle changes to -178.4 deg.The absolute conformation around the styrene-like arrangement of the bonds in 15-21 can be deduced from the strong positive Cotton effect at ca. 350 nm.Cyclopropanation of styrene with ethyl diazoacetate, in the presence of in situ generated Cu(I) complexes of chiral 1,5-bidentate ligands 15-21, yielded cis/trans 2-phenylcyclopropan-1-carboxylic acid ethylesters with 5-21percent e.e.Though generally low, the enantioselectivity was somewhat higher for ortho-(16-18) than for para-(19-21) substituted phenyl derivatives.

CONVENIENT METHOD FOR THE PREPARATION OF 2-PHENACYLPYRIDINES

2-Phenacylpyridines (3) were prepared from 2-(trimethylsilylmethyl)pyridine (1) and p-substituted benzonitriles (2) (X = H, Cl CH3, OCH3) in high yields (70 ca. 90percent)under a mild condition (LDA/THF, -75 deg C).The method was compared with a reaction of α-picoline with (2) under the same condition.The keto-enol tautomerism of (3) were also discussed by means of the nmr spectra.