2-Acetylpyridine

Base Information

• Chemical Name: 2-Acetylpyridine
• CAS No.: 1122-62-9
• Molecular Formula: C7H7NO
• Molecular Weight: 121.139
• Hs Code.: 29333999
• European Community (EC) Number: 214-355-6
• NSC Number: 15043
• UNII: 629O10UI3L
• DSSTox Substance ID: DTXSID7024409
• Nikkaji Number: J71.242F
• Wikipedia: 2-Acetylpyridine
• Wikidata: Q4596853
• Metabolomics Workbench ID: 46905
• ChEMBL ID: CHEMBL11945
• Mol file: 1122-62-9.mol

Synonyms:2-acetylpyridine;methyl 2-pyridyl ketone

Chemical Property of 2-Acetylpyridine

Chemical Property:

• Appearance/Colour: clear colorless to slightly brown liquid
• Vapor Pressure: 0.481mmHg at 25°C
• Melting Point: 8-10 ºC
• Refractive Index: n20/D 1.521(lit.)
• Boiling Point: 192.8 ºC at 760 mmHg
• PKA: pK1: 2.643(+1) (25°C)
• Flash Point: 73.3 ºC
• PSA: 29.96000
• Density: 1.06 g/cm³
• LogP: 1.28420
• Storage Temp.: Store below +30°C.
• Solubility.: 170g/l
• Water Solubility.: Soluble in water (18.2 g/100g @ 25C). Soluble in and acetate. Slightly soluble in carbon tetrachloride.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 121.052763847
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

98% ^*data from raw suppliers

2-Acetylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-38
• Safety Statements: 26-36-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC(=O)C1=CC=CC=N1
• Chemical Structure: 2-Acetylpyridine is an aromatic ketone with the molecular structure consists of a pyridine ring with a ketone group attached at the 2-position.
• Uses: 2-Acetylpyridine has been utilized in the synthesis of metal complexes for several decades, with recent research focusing on its antitumor properties. It is used in the synthesis of novel antitumor agents derived from benzoxazol-2-yl and benzimidazol-2-yl hydrazones. It's role in antitumor activity involves inhibition of cell proliferation in various cancer cell lines.
• References: [1] Spectral characterization of metal complexes derived from glycine (Gly) and 2-acetylpyridine (2-APy); DOI 10.1016/j.molstruc.2011.06.019; [2] Interesting copper(ii)-assisted transformations of 2-acetylpyridine and 2-benzoylpyridine; DOI 10.1039/C5DT03912F; [3] 2-benzoxazolyl and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine: A novel class of antitumor agents; DOI 10.1002/ijc.1427

Technology Process of 2-Acetylpyridine

There total 72 articles about 2-Acetylpyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-acetylpyridine N-oxide (2457-50-3) → 2-acetylpyridine (1122-62-9)

Guidance literature:

With cis-Cyclooctene; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI); In benzene; at 80 ℃; for 15h;

DOI:10.1248/cpb.46.1656

Reference yield: 94.0%

1-(pyridine-2-yl)ethanol (20988-55-0,18728-61-5,27911-63-3,59042-90-9) → 2-acetylpyridine (1122-62-9)

Guidance literature:

With 9-azabicyclo[3.3.1]nonan-3-one N-oxyl oxide; oxygen; nitric acid; sodium nitrite; In acetonitrile; at 20 ℃; for 3h; under 760.051 Torr; Reagent/catalyst; Solvent;

DOI:10.1021/cs400746m

Reference yield: 94.0%

2-Picolinic acid (98-98-6) + methyllithium (917-54-4) → 2-acetylpyridine (1122-62-9)

Guidance literature:

methyllithium; With copper(l) cyanide; In diethyl ether; at 0 ℃; for 0.0833333h; Inert atmosphere;

2-Picolinic acid; In diethyl ether; at 0 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ol202237j

upstream raw materials:

2-vinylpyridine

2-Cyanopyridine

methyl magnesium iodide

ethyl-2-picolinate

Downstream raw materials:

1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide

2-[2]pyridyl-butan-2-ol

2-(pyridin-2-yl)-quinoline-4-carboxylic acid

(E)-3-(3-nitrophenyl)-1-(pyridin-2-yl)prop-2-en-1-one

Refernces

Ruthenium(II) complexes containing N(4)-tolyl-2-acetylpyridine thiosemicarbazones and phosphine ligands: NMR and electrochemical studies of cis-trans isomerization

10.1016/j.molstruc.2007.04.032

The research study on ruthenium(II) complexes containing N(4)-tolyl-2-acetylpyridine thiosemicarbazones and phosphine ligands, focusing on their NMR and electrochemical properties, particularly the cis-trans isomerization process. The purpose of the study was to investigate the pharmacological versatility of these complexes, considering their potential antitumor properties. The researchers synthesized three complexes, [Ru(H2Ac4oT)(PPh3)2Cl]Cl (1), [Ru(H2Ac4mT)(PPh3)2Cl]Cl (2), and [Ru(H2Ac4pT)(PPh3)2Cl]Cl (3), using thiosemicarbazones derived from 2-formyl and 2-acetylpyridine, and triphenylphosphine as ligands. The conclusions drawn from the study indicate that both cis and trans isomers exist in solution, with the cis isomers converting into trans isomers over time.

Shape-persistent, ruthenium(ii)- and iron(ii)-bisterpyridine metallodendrimers: Synthesis, traveling-wave ion-mobility mass spectrometry, and photophysical properties

10.1039/c2nj20799k

The study focuses on the synthesis, characterization, and investigation of the photophysical and electrochemical properties of shape-persistent metallodendrimers based on htpy-RuII-tpyi or htpy-FeII-tpyi connectivity. These metallodendrimers were developed using a self-assembly strategy and were fully characterized by techniques such as 1H and 13C NMR, traveling wave ion mobility mass spectrometry (TWIM MS), single crystal X-ray, UV-vis absorption, photoluminescence, and cyclic voltammetry. The researchers observed a significant increase in drift times with increasing generation of these complexes, correlating with the change in molecular size. Additionally, the photophysical properties, such as molar extinction coefficients, and electrochemical stability of the complexes varied noticeably with size and metal ion center, suggesting potential applications in catalysis, sensing, and light-harvesting devices.