2,4,6-Collidine Chemical Properties

Melting point:

-43 °C (lit.)

Boiling point:

171-172 °C (lit.)

Density 

0.917 g/mL at 25 °C (lit.)

vapor pressure 

4 hPa (20 °C)

refractive index 

n20/D 1.498(lit.)

Flash point:

135 °F

storage temp. 

Store below +30°C.

solubility 

35g/l

form 

Liquid

pka

7.43(at 25℃)

color 

Clear colorless to yellow

Water Solubility 

35 g/L (20 ºC)

Sensitive 

Hygroscopic

Merck 

14,9718

BRN 

107283

Dielectric constant

1.9（20℃）

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

LogP

1.25 at 20℃

CAS DataBase Reference

108-75-8(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 2,4,6-trimethyl-(108-75-8)

EPA Substance Registry System

2,4,6-Trimethylpyridine (108-75-8)

Safety Information

Hazard Codes 

Xn

Risk 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

HS Code 

29333999

Hazardous Substances Data

108-75-8(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 400 mg/kg

MSDS

• Language:English Provider:2,4,6-Trimethylpyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,4,6-Collidine Usage And Synthesis

Chemical Properties

colourless liquid

Uses

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.

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.

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.]

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