4-Acetylpyridine

Base Information

• Chemical Name: 4-Acetylpyridine
• CAS No.: 1122-54-9
• Molecular Formula: C7H7NO
• Molecular Weight: 122.147
• Hs Code.: 29333999
• European Community (EC) Number: 214-350-9
• NSC Number: 111
• UN Number: 2810
• UNII: G47437IOW7
• DSSTox Substance ID: DTXSID0022147
• Nikkaji Number: J41.571E
• Wikidata: Q27278737
• ChEMBL ID: CHEMBL445953
• Mol file: 1122-54-9.mol

Synonyms:4-acetylpyridine

Chemical Property of 4-Acetylpyridine

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid.
• Vapor Pressure: 0.17mmHg at 25°C
• Melting Point: 13-16 °C(lit.)
• Refractive Index: n20/D 1.529(lit.)
• Boiling Point: 212.8 °C at 760 mmHg
• PKA: pK1: 3.505(+1) (25°C)
• Flash Point: 87 °C
• PSA: 29.96000
• Density: 1.095 g/cm³
• LogP: 1.28420
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: insoluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 121.052763847
• Heavy Atom Count: 9
• Complexity: 106
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Acetylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC=NC=C1
• Uses: 4-Acetylpyridine is a acetylated pyridine used in the preparation of nitrogen containing bicyclic heterocycles and other organic compounds. 4-Acetylpyridine is also present in mainstream cigarette smo ke. 4-acetylpyridine on reaction with - and 4-formylpyridine (H3FoPyS, H4FoPyS) yields semicarbazones. Reaction of acetylpyridine with thiophene-2-carboxaldehyde afforded the 2-chloro-6-ethoxy-4-β-(2-thienyl)acryloylpyridine, which was reacted with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to afford the cyanoaminopyrane derivative.

Technology Process of 4-Acetylpyridine

There total 66 articles about 4-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%

4-pyridylacetylene (2510-22-7) → methyl (4-pyridyl) ketone (1122-54-9)

Guidance literature:

With cobalt(III)((CH₂NCHC₆H₄(O))2)(OAc); sulfuric acid; In methanol; water; at 80 ℃; for 20h; Schlenk technique;

DOI:10.1002/cctc.201400071

Reference yield: 97.0%

2,5-bis-(4-pyridyl)-3,4-diaza-2,4-hexadiene → methyl (4-pyridyl) ketone (1122-54-9)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1080/00397919908086590

Reference yield: 96.0%

N-phenyl-N'-(1-pyridin-4-yl-ethylidene)hydrazine → methyl (4-pyridyl) ketone (1122-54-9)

Guidance literature:

With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate; In acetonitrile; for 0.75h; Heating;

DOI:10.1246/bcsj.71.2655

upstream raw materials:

4-Ethylpyridine

pyridine-4-carbonitrile

methyl magnesium iodide

isonicotinic acid ethylester

Downstream raw materials:

1-(morpholin-4-yl)-2-(pyridin-4-yl)ethanethione

isonicotinic acid-(1-[4]pyridyl-ethylidenehydrazide)

1,3-bis(pyridin-4-yl)propane-1,3-dione

4,4,4-trifluoro-1-(pyridin-4-yl)butane-1,3-dione

Refernces

• 1、 Frassoldati, Antonio,Pinel, Catherine,Besson, Michèle. "Aerobic oxidation of secondary pyridine-derivative alcohols in the presence of carbon-supported noble metal catalysts". . p. 133 - 138. Retrieved 2013.
• 2、 Gao, Xianying,Han, Shuaijun,Zheng, Maolin,Liang, Apeng,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie,Li, Jingya. "Transition-Metal-Free Oxidation of Benzylic C-H Bonds of Six-Membered N-Heteroaromatic Compounds". . p. 4040 - 4049. Retrieved 2019.
• 3、 Tero-Kubota, Shozo,Akiyama, Kimio,Ikoma, Tadaaki,Ikegami, Yusaku. "Time-Resolved EPR Studies on the Photochemical Hydrogen Abstraction Reactions and the Excited Triplet States of 4-Substituted Pyridines". . p. 766 - 770. Retrieved 1991.
• 4、 Shimoyama, Yoshihiro,Kitagawa, Yasutaka,Ohgomori, Yuji,Kon, Yoshihiro,Hong, Dachao. "Formate-driven catalysis and mechanism of an iridium-copper complex for selective aerobic oxidation of aromatic olefins in water". . p. 5796 - 5803. Retrieved 2021.
• 5、 Gleich, Edward,Warnke, Zygmunt. "Elemental selenium reactions with 4-ethylpyridine". . p. 13 - 28. Retrieved 1998.
• 6、 Choudhury, Prabhupada,Behera, Pradyota Kumar,Bisoyi, Tanmayee,Sahu, Santosh Kumar,Sahu, Rashmi Ranjan,Prusty, Smruti Ranjita,Stitgen, Abigail,Scanlon, Joseph,Kar, Manoranjan,Rout, Laxmidhar. "The dehydrogenative oxidation of aryl methanols using an oxygen bridged [Cu-O-Se] bimetallic catalyst". . p. 5775 - 5779. Retrieved 2021.
• 7、 Pei, Wen,Mo, Jun,Xiao, Jianliang. "Highly regioselective Heck reactions of heteroaryl halides with electron-rich olefins in ionic liquid". . p. 3546 - 3551. Retrieved 2005.
• 8、 Bu, Hongzhong,Gu, Jiefan,Li, Yufeng,Ma, Hongfei,Wan, Yuting,Wu, Zheng-Guang,Zhang, Weijian,Zhou, Ying'ao,Zhu, Hongjun. "Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion". . . Retrieved 2021/07/16.
• 9、 Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin. "Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls". supporting information. p. 7445 - 7449. Retrieved 2021/10/02.