2,4,6-Trimethylpyridine

Base Information

• Chemical Name: 2,4,6-Trimethylpyridine
• CAS No.: 108-75-8
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 29333999
• European Community (EC) Number: 203-613-3
• NSC Number: 460
• UN Number: 1993
• UNII: 7IE4BK5J5V
• DSSTox Substance ID: DTXSID1051561
• Nikkaji Number: J5.079B
• Wikipedia: 2,4,6-Trimethylpyridine
• Wikidata: Q409155
• ChEMBL ID: CHEMBL1209580
• Mol file: 108-75-8.mol

Synonyms:2,4,6-trimethylpyridine;collidine;gamma-collidine

Chemical Property of 2,4,6-Trimethylpyridine

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 1.9mmHg at 25°C
• Melting Point: -43 °C(lit.)
• Refractive Index: n20/D 1.498(lit.)
• Boiling Point: 171 °C at 760 mmHg
• PKA: 7.43(at 25℃)
• Flash Point: 57.2 °C
• PSA: 12.89000
• Density: 0.917 g/cm³
• LogP: 2.00680
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: 35g/l
• Water Solubility.: 35 g/L (20 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 80.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2,4,6-Collidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC1=CC(=NC(=C1)C)C
• Uses: 2,4,6-Collidine is an reagent used for various synthetic preparations such as the synthesis of methylated pyridines by three-componet catalytic condensation of acetylene, acetone and ammonia. 2,4,6-Collidine is used as a tissue fixative for electron microscopy. It is useful in dehydrohalogenation reactions and acts as a solvent for the cleavage of hindered esters by anhydrous lithium iodide.

Technology Process of 2,4,6-Trimethylpyridine

There total 116 articles about 2,4,6-Trimethylpyridine 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: 90.0%

1-(N-Phenyl-N-methylamino)-2,4,6-trimethylpyridinium perchlorate → 2,4,6-trimethyl-pyridine (108-75-8) + N-methylaniline (100-61-8)

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; preparative electrolyse, - 1.4 V;

Reference yield: 87.0%

1-Ethoxycarbonylamino-2,4,6-trimethyl-pyridinium; perchlorate → 2,4,6-trimethyl-pyridine (108-75-8) + C11H16N2O2 + urethane (51-79-6)

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; preparative electrolyse, - 2.3 V;

Reference yield: 69.0%

1-Benzoylamino-2,4,6-trimethylpyridinium perchlorate → 2,4,6-trimethyl-pyridine (108-75-8) + benzamide (55-21-0,27208-38-4) + benzonitrile (100-47-0)

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; preparative electrolyse, - 1.4 V;

upstream raw materials:

2,6-dimethylpyridine

2,2,4,6-tetramethyl-2,3-dihydropyridine

3,5-dimethyl-2-cyclohexen-1-one

3-Methylbutenoic acid

Downstream raw materials:

3β-benzoyloxycholesta-5,7-diene

2-(4,6-dimethylpyridin-2-yl)ethanol

4,6-dimethyl-2-vinylpyridine

2-(2,6-dimethyl-[4]pyridyl)-propane-1,3-diol

Refernces

• 1、 Morimoto, Yoshiki,Kurihara, Hajime,Yokoe, Chiho,Kinoshita, Takamasa. "New aspect of methanesulfonyl chloride: Unusual deoxygenations of pyridine N-oxides with methanesulfonyl chloride and triethylamine". . p. 829 - 830. Retrieved 1998.
• 2、 Arnaud et al.. "-". . p. 2972,2973, 2976. Retrieved 1979.
• 3、 Neverov, Alexei A.,Brown. "Mechanistic Evaluation of the Transfer of Br+ from Bis(sym-collidine)bromonium Triflate to Acceptor Alkenes". . p. 5977 - 5982. Retrieved 1998.
• 4、 Jasinski, Joseph M.,Brauman, John I.. "Rates of Proton Transfer between Pyridine Bases in the Gas Phase. Steric and Isotope Effects". . p. 2906 - 2913. Retrieved 1980.
• 5、 -. "NOVEL METHODS FOR PREPARATION OF SUBSTITUTED PYRIDINES AND RELATED NOVEL COMPOUNDS". Paragraph 0195; 0218; 0219. . Retrieved 2020/04/10.
• 6、 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 2018/07/06.