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

4'-(4''-pyridyl)-2,2':6',2''-terpyridine

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

3-(furan-2-yl)-1-(pyridin-2-yl)prop-2-en-1-one

Refernces

• 1、 Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola,Poli, Silvia,Sinigaglia, Milena. "Kinetic Resolution of 1-Aryl- and 1-Heteroaryl Ethanols by Oxidation with Baker's Yeast". . p. 883 - 884. Retrieved 1993.
• 2、 Walker. "-". . p. 1047,1048. Retrieved 1960.
• 3、 Verhoeven, Dide G. A.,Albrecht, Martin. "Modular O-: Vs. N-coordination of pyridylidene amide ligands to iron determines activity in alcohol oxidation catalysis". . p. 17674 - 17682. Retrieved 2020.
• 4、 Gowda, Maravanhalli Sidde,Pande, Sushanth Sudhir,Ramakrishna, Ramesha Andagar,Prabhu, Kandikere Ramaiah. "Acylation of Grignard reagents mediated by N-methylpyrrolidone: A remarkable selectivity for the synthesis of ketones". . p. 5365 - 5368. Retrieved 2011.
• 5、 Larsen, Dennis,Pittelkow, Michael,Karmakar, Saswata,Kool, Eric T.. "New Organocatalyst scaffolds with high activity in promoting hydrazone and oxime formation at neutral pH". . p. 274 - 277. Retrieved 2015.
• 6、 Miyamura, Hiroyuki,Matsubara, Ryosuke,Kobayashi, Shu. "Gold-platinum bimetallic clusters for aerobic oxidation of alcohols under ambient conditions". . p. 2031 - 2033. Retrieved 2008.
• 7、 Mitsudome, Takato,Noujima, Akifumi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Efficient aerobic oxidation of alcohols using a hydrotalcitesupported gold nanoparticle catalyst". . p. 1890 - 1896. Retrieved 2009.
• 8、 Ma, Shuai,Cui, Jing-Wang,Rao, Cai-Hui,Jia, Meng-Ze,Chen, Yun-Rui,Zhang, Jie. "Boosting activity of molecular oxygen by pyridinium-based photocatalysts for metal-free alcohol oxidation". . p. 1337 - 1343. Retrieved 2021.
• 9、 Duan, Limei,Li, Peihe,Li, Wanfei,Liu, Jinghai,Liu, Ying,Liu, Zhifei,Lu, Ye,Sarina, Sarina,Wang, Jinghui,Wang, Yin,Wang, Yingying,Zhu, Huaiyong. "Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride". . p. 4429 - 4438. Retrieved 2021/07/12.