108-75-8

Basic information

• Product Name: 2,4,6-Collidine
• Synonyms: 2,4,6-Kollidin;2,4,6-trimethyl-pyridin;a,g,a'-Collidine;alpha,gamma,alpha’-collidine;alpha,gamma,alpha'-Collidine;g-Collidine;Pyridine,2,4,6-trimethyl-;S-COLLIDINE
• CAS NO: 108-75-8
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• EINECS: 203-613-3
• Product Categories: Heterocyclic Compounds
• Mol File: 108-75-8.mol
• Article Data: 47

Chemical Properties

• Melting Point: −43 °C(lit.)
• Boiling Point: 171-172 °C(lit.)
• Flash Point: 135 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.917 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.9mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Storage Temp.: 2-8°C
• Solubility: 35g/l
• PKA: 7.43(at 25℃)
• Water Solubility: 35 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,9718
• BRN: 107283
• CAS DataBase Reference: 2,4,6-Collidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Collidine(108-75-8)
• EPA Substance Registry System: 2,4,6-Collidine(108-75-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 26-36/37-36
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 3
• RTECS: UU0970000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 108-75-8(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 108-75-8 differently. You can refer to the following data:
1. 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. 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.

Definition

Methyl, ethyl, propyl, and trimethyl homologs of pyridine.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 4184, 1950 DOI: 10.1021/ja01165a097

General Description

2,4,6-Trimethylpyridine is a pyridine derivative. It has a pK of 7.4. The product can react with trifluoroiodomethane in cyclopentane solution to afford 1:1 complex. This complex was investigated by NMR (Nuclear Magnetic Resonance) spectroscopy. Collidine-buffered osmium tetroxide solutions have been prepared by adding osmium tetroxide solution to it. These solutions have been used as fixative for electron microscopic studies.2,4,6-Trimethylpyridine can undergo oxidation with potassium permanganate to form 2,4,6-pyridinetricarboxylic acid.

Hazard

Toxic.

Flammability and Explosibility

Flammable

Purification Methods

Commercial samples may be grossly impure. Likely contaminants include 3,5-dimethylpyridine, 2,3,6-trimethylpyridine and water. Brown, Johnson and Podall [J Am Chem Soc 76 5556 1954] fractionally distilled 2,4,6-trimethylpyridine under reduced pressure through a 40cm Vigreux column (p 11) and added to 430mL of the distillate slowly, with cooling to 0o, 45g of BF3-diethyl etherate. The mixture was again distilled, and an equal volume of dry *benzene was added to the distillate. Dry HCl was passed into the solution, which was kept cold in an ice-bath, and the hydrochloride was filtered off. It was recrystallised from absolute EtOH (1.5mL/g) to m 286-287o[m 256o(sealed tube), also m 293-294o subliming slowly]. The free base was regenerated by treatment with aqueous NaOH, then extracted with *benzene, dried (MgSO4) and distilled under reduced pressure. Sisler et al. [J Am Chem Soc 75 446 1953] precipitated trimethylpyridine as its phosphate from a solution of the base in MeOH by adding 85% H3PO4, shaking and cooling. The free base was regenerated as above. Garrett and Smythe [J Chem Soc 763 1903] purified the trimethylpyridine via the HgCl2 complex. It is more soluble in cold than hot H2O [the solubility is 20.8% at 6o, 3.5% at 20o, 1.8% at 100o]. Alternatively, purify it by dissolving it in CHCl3, adding solid K2CO3 and Drierite, filtering and fractionally distilling through an 8in helix-packed column. The sulfate has m 205o, and the picrate (from hot H2O) has m 155-156o. [Frank & Meikle J Am Chem Soc 72 4184 1950, Beilstein 20 H 250, 20 I 87, 20 II 164, 20 III/IV 2810, 20/6 V 93.]

InChI:InChI=1/C8H11N/c1-6-4-7(2)9-8(3)5-6/h4-5H,1-3H3

Upstream product

• 541-47-9 3-Methylbutenoic acid 
• 940-93-2 2,4,6-trimethylpyrylium chlorate(VII) 
• 3376-50-9 2,4,6-trimethyl-pyridine 1-oxide 
• 77287-34-4 formamide 
• 17523-60-3 2,4,6-Trimethylpyridiniumkation 
• 54219-44-2 naphthalene-1,4-diol; deprotonated form 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 108-24-7 acetic anhydride 
• 13905-13-0 2,5-dimethyl-hex-4-en-3-one 
• 13905-10-7 5-methyl-4-hexen-3-one 
• 6148-01-2 2,4,6-trimethylpyridinium picrate 
• 764-01-2 methyl propargyl alcohol 
• 75-07-0 acetaldehyde 
• 67-64-1 acetone 

Downstream Products

• 1182-06-5 3β-benzoyloxycholesta-5,7-diene 
• 13287-63-3 2-(4,6-dimethylpyridin-2-yl)ethanol 
• 13959-30-3 4,6-dimethyl-2-vinylpyridine 
• 13959-27-8 2-(2,6-dimethyl-[4]pyridyl)-propane-1,3-diol 
• 119073-19-7 bis-[2-(2,6-dimethyl-[4]pyridyl)-3-hydroxy-2-hydroxymethyl-propoxy]-methane 
• 646-30-0 nonadecanoic acid 
• 1162-56-7 6-dehydroprogesterone 
• 99075-35-1 carbamic acid-(1-cyclohex-3-enyl-prop-2-yn-1-yl ester) 
• 108-95-2 phenol 
• 434-16-2 7-dehydrocholesterol 
• 6553-64-6 6,6-Dimethyl-2-cyclohexen-1-one 
• 601-57-0 Cholest-4-en-3-one 
• 601-55-8 5α-cholest-1-en-3-one 
• 73982-28-2 6,6-diphenylcyclohex-2-en-1-one 

Related news

New stable atropisomers derived from 2,4,6-Collidine (cas 108-75-8) and related compounds08/19/2019

The Suzuki–Miyaura cross-coupling reaction of 3,5-dibromo-2,4,6-collidine and bromo derivatives of 2,6- and 2,4-lutidine with several ortho-substituted boronic acids produced a library of arylated pyridines. The reaction conditions were carefully optimized to allow high yield of the desired pro...detailed

Relevant articles and documents

TETRAACYLATION OF ISOBUTENE : FIRST SYNTHESIS OF 1,3,6,8-TETRAMETHYL-2,7-NAPHTHYRIDINE

The tetraacetylation of isobutene has been performed in AlCl3/AcCl.Treatment of the crude reaction medium with liquid ammonia yields the title compound.

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SYNTHESIS AND PROPERTIES OF BIS(PYRIDYLMETHYLENE)MERCURY DERIVATIVES

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The reduction of several aromatic nitro compounds to amines by means of the two novel catalytic systems ([IMes]2ReOBr3)/PhSiH3 and ([Py]3ReNOBr2)/PhSiH3 under microwave irradiation is here reported. These two systems were able to perform the reduction of nitro groups with higher TON and TOF when compared with previously reported systems based on oxo-rhenium core under standard heating, although they showed a lesser broad reaction scope compared with the known systems.

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The present invention provides a supercritical fluid technology based on 2, 4, 6 - trimethyl pyridine production method, comprising the following steps: adding the catalyst and acetone in the supercritical reaction vessel, stir, the liquid ammonia into the reactor, first pressurizing and heating make the liquid ammonia to achieve the ultra zero state, and then to continue to pressurizing and heating the acetone to achieve ultra zero state, rapid cooling, the termination of the reaction, based on supercritical fluid technology to obtain 2, 4, 6 - trimethyl pyridine elementary product; or the acetone added supercritical in the reactor, the liquid ammonia into the reactor, first pressurizing and heating make the liquid ammonia to achieve the ultra zero state, and then to continue to pressurizing and heating the acetone to achieve ultra zero state, rapid cooling, the termination of the reaction, based on supercritical fluid technology to obtain 2, 4, 6 - trimethyl pyridine and taste; finally the 2, 4, 6 - trimethyl pyridine elementary product through the rectification, based on supercritical fluid technology to obtain 2, 4, 6 - trimethyl pyridine. Preparation method of this invention is simple, efficient reaction, the yield of the product and high purity. (by machine translation)

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH

Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.