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

Reagent-controlled stereoselectivity in titanocene-catalyzed epoxide openings: Reductions and intermolecular additions to α,β-unsaturated carbonyl compounds

10.1002/chem.200390056

The study focuses on the stereoselective reactions of titanocene-catalyzed epoxide openings, investigating the control of enantioselectivity and diastereoselectivity through variations in metal complex ligands. The research explores the generation and addition reactions of metal-bound radicals derived from both normal and meso epoxides, utilizing electron transfer from titanocene(III) reagents. The study aims to develop synthetically useful alcohols through highly selective reactions while avoiding the use of toxic metals and the loss of functional groups often observed in reductive radical chain reactions. Key chemicals used include various titanocene complexes as catalysts, epoxides as radical precursors, and reagents like zinc, collidine, and acrylates to facilitate the reactions. The purpose of these chemicals is to achieve unprecedented selectivity in radical reactions, providing a complementary approach to other enantioselective catalytic radical reactions.

10.1021/jo00822a019

The research explores the conversion of 1,3-dithiane derivatives to carbonyl compounds through oxidative hydrolysis using N-halosuccinimide reagents. The study aims to develop specific and effective procedures for this conversion, which is significant in the synthesis and interconversion of monocarbonyl and 1,3-dicarbonyl compounds. The researchers found that mercury(II)-promoted hydrolysis is effective for 2,2-dialkyl derivatives but less so for 2-monoalkyl and 2-acyl derivatives. To address this, they devised three N-halosuccinimide reagents—N-bromosuccinimide alone, N-bromosuccinimide with silver ion, and N-chlorosuccinimide with silver ion—which efficiently hydrolyze 2-acyl-1,3-dithianes to 1,2-dicarbonyl compounds, significantly extending the synthetic utility of the lithiodithiane method. The study concludes that these reagents, particularly N-chlorosuccinimide with silver ion, are advantageous for unsaturated dithianes as they do not affect olefinic linkages, and they can be buffered with 2,6-lutidine or 2,4,6-collidine for acid-sensitive substrates, yielding aldehydes and ketones in high percentages (70-100%).