4-Picoline-N-oxide

Base Information

• Chemical Name: 4-Picoline-N-oxide
• CAS No.: 1003-67-4
• Deprecated CAS: 117889-41-5,344242-54-2,1084930-90-4,1197996-56-7,1084930-90-4,1197996-56-7,344242-54-2
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 29333999
• European Community (EC) Number: 213-712-3
• NSC Number: 141449,5086
• UNII: QIY3009LEH
• DSSTox Substance ID: DTXSID8061393
• Nikkaji Number: J31.406D
• Wikidata: Q27287286
• Mol file: 1003-67-4.mol

Synonyms:4-Picoline,1-oxide (6CI,8CI);4-Methylpyridine 1-oxide;4-Methylpyridine N-oxide;4-Methylpyridine oxide;4-Picoline N-oxide;4-Picoline oxide;NSC 5086;g-Picoline 1-oxide;g-Picoline N-oxide;g-Picoline oxide;N-oxide of 4-methyl pyridine;

Chemical Property of 4-Picoline-N-oxide

Chemical Property:

• Appearance/Colour: Almost white to brown fine crystalline powder
• Vapor Pressure: 0.00692mmHg at 25°C
• Melting Point: 182-185 °C(lit.)
• Refractive Index: 1.512
• Boiling Point: 279.2 °C at 760 mmHg
• PKA: 1.38±0.10(Predicted)
• Flash Point: 122.6 °C
• PSA: 25.46000
• Density: 1.01 g/cm³
• LogP: 1.42350
• Storage Temp.: Store at +2°C to +8°C.
• Sensitive.: Hygroscopic
• Solubility.: 1000g/l
• Water Solubility.: soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 66.9

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Picoline-N-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amine Oxides
• Canonical SMILES: CC1=CC=[N+](C=C1)[O-]

Technology Process of 4-Picoline-N-oxide

There total 41 articles about 4-Picoline-N-oxide 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%

picoline (108-89-4) → 4-methylpyridine-1-oxide (1003-67-4)

Guidance literature:

With dihydrogen peroxide; In water; at 90 ℃; for 1h; Reflux;

DOI:10.1080/00397911.2011.628134

Reference yield: 35.0%

picoline (108-89-4) + perfluoro-cis-2-n-butyl-3-n-propyloxaziridine → 4-methylpyridine-1-oxide (1003-67-4) + 4-Methyl-N-(perfluorobutanoyl)pyridinium-1-aminide

Guidance literature:

In chloroform; trichlorofluoromethane; at -60 ℃; for 0.5h;

DOI:10.1039/p19960002517

Reference yield: 35.0%

picoline (108-89-4) → 4-methylpyridine-1-oxide (1003-67-4) + 4-Methyl-N-(perfluorobutanoyl)pyridinium-1-aminide

Guidance literature:

With perfluoro(cis-2-butyl-3-propyloxaziridine); In chloroform; trichlorofluoromethane; at -60 ℃; for 0.5h;

DOI:10.1039/p19960002517

upstream raw materials:

picoline

dibenzoyl peroxide

4-methylpyridine N-oxide hemiperchlorate

Trifluoro-methanesulfonate4-methyl-1-trifluoromethanesulfonyloxy-pyridinium;

Downstream raw materials:

4-methylpyridin-3-ol

4-acetoxymethylpyridine

4-(4-methyl-trans-styryl)-pyridine-1-oxide

4-(α-styryl)pyridine 1-oxide

Refernces

• 1、 Khatri, Praveen K.,Choudhary, Shivani,Singh, Raghuvir,Jain, Suman L.,Khatri, Om P.. "Grafting of a rhenium-oxo complex on Schiff base functionalized graphene oxide: An efficient catalyst for the oxidation of amines". . p. 8054 - 8061. Retrieved 2014.
• 2、 Schie?l, Jasmin,Stein, Philipp M.,Stirn, Judith,Emler, Kirsten,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.. "Strategic Approach on N-Oxides in Gold Catalysis – A Case Study". . p. 725 - 738. Retrieved 2019.
• 3、 Al-Arnaout, A.,Courtois, G.,Miginiac, L.. "Synthese regioselective par voie organometallique de pyridines, 4-picolines et 3,5-lutidines substituees en 2 par un groupe insature et/ou fonctionnel". . p. 139 - 154. Retrieved 1987.
• 4、 Jain, Suman L.,Sain, Bir. "Ruthenium catalyzed oxidation of tertiary nitrogen compounds with molecular oxygen: An easy access to N-oxides under mild conditions". . p. 1040 - 1041. Retrieved 2002.
• 5、 Kotowski, Mirjana,Marcec, Radovan,Butkovic, Vjera,Bakac, Andreja,Orhanovic, Matko. "Preparation, characterization, and aquation kinetics of pyridine N-oxide complexes of chromium(III)". . p. 2894 - 2899. Retrieved 2006.
• 6、 Rybachenko,Chotii,Kovalenko,Schroeder. "Equilibrium of acetyl transfer between pyridine N-Oxides and their acetylonium salts". . p. 786 - 788. Retrieved 2001.
• 7、 Hu, Rui-Xiang,Huang, Ling,Liang, Hong,Yu, Kai-Bei. "Hydrogen bonding network assembled with 2-amino-3-hydroxypyridium and isonicotinate-N-oxide". . p. 523 - 526. Retrieved 2007.
• 8、 Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Hezarkhani, Hadis Afshar. "A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate". . p. 1843 - 1849. Retrieved 2018.
• 9、 Yang, Chunxia,Zhao, Wei,Cheng, Zhiguo,Luo, Baomin,Bi, Dongqin. "Catalytic system for pyridine oxidation to N-oxides under mild conditions based on polyoxomolybdate". . p. 36809 - 36812. Retrieved 2015.
• 10、 Dongre,Venkateshwar Rao,Sharma,Sain,Bhatia. "Oxidation of tertiary nitrogen compounds to N-oxides by molecular oxygen-aldehyde system in the absence of metal catalyst". . p. 167 - 172. Retrieved 2001.