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HomeProduct name list2,4,6-Collidine

2,4,6-Collidine

Synonym(s):sym-Collidine;2,4,6-Collidine;2,4,6-Trimethylpyridine;sym.-Collidine

  • CAS NO.:108-75-8
  • Empirical Formula: C8H11N
  • Molecular Weight: 121.18
  • MDL number: MFCD00006338
  • EINECS: 203-613-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:15:30
2,4,6-Collidine Structural

What is 2,4,6-Collidine?

Chemical properties

colourless liquid

The Uses of 2,4,6-Collidine

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.

The Uses of 2,4,6-Collidine

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.]

Properties of 2,4,6-Collidine

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.
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 for 2,4,6-Collidine

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H226:Flammable liquids
H311:Acute toxicity,dermal
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2,4,6-Collidine

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