2,4,6-Collidine

2,4,6-Collidine 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-;2 Minus 2-3 Methyl pyridine
CAS:108-75-8
MF:C8H11N
MW:121.18
EINECS:203-613-3
Product Categories:Heterocyclic Compounds;bc0001;108-75-8
Mol File:108-75-8.mol
2,4,6-Collidine Structure
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.)
Fp 135 °F
storage temp. Store below +30°C.
solubility 35g/l
form Liquid
pka7.43(at 25℃)
color Clear colorless to yellow
Water Solubility 35 g/L (20 ºC)
Sensitive Hygroscopic
Merck 14,9718
BRN 107283
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
LogP1.25 at 20℃
CAS DataBase Reference108-75-8(CAS DataBase Reference)
NIST Chemistry ReferencePyridine, 2,4,6-trimethyl-(108-75-8)
EPA Substance Registry System2,4,6-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 Data108-75-8(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 400 mg/kg
MSDS Information
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2,4,6-Trimethylpyridine English
SigmaAldrich English
ACROS English
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2,4,6-Collidine Usage And Synthesis
Chemical Propertiescolourless liquid
Uses2,4,6-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.
Uses2,4,6-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.
DefinitionMethyl, 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 Description2,4,6-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.
HazardToxic.
Flammability and ExplosibilityFlammable
Purification MethodsCommercial 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.]
trimethylpyridine,MIX-COLLIDINE,collidine(combustibleliquid,n.o.s. 2.4.6-TRIMETHYL-3-NITROPYRIDINE 2,6-Di-tert-butyl-4-methylpyridine 2,3,5-COLLIDINE,2,3,5-COLLIDINE 2,3,5-TRIMETHYLPYRIDINE,2,3,5-Collidine, 99+%,2,3,5-COLLIDINE 2,3,5-TRIMETHYLPYRIDINE,2,3,5-TRIMETHYLPYRIDINE Streptonigrin 1-FLUORO-2,4,6-TRIMETHYLPYRIDINIUM TRIFLATE 2-Chloro-5-chloromethylpyridine 2-(4-CHLOROPHENYL)-6-(4-METHOXYPHENYL)-4-PHENYLPYRIDINE 4-Methylpyridine 3-Acetyl-2,4,6-trimethylpyridine DIMETHYL 4-(4-METHOXYPHENYL)-2,6-DIMETHYLPYRIDINE-3,5-DICARBOXYLATE HYDROGEN FLUORIDE 2,4,6-COLLIDINE COMPLEX 2-(4-METHOXYPHENYL)-4-PHENYL-6-(4-TOLYL)PYRIDINE Azamethiphos Pyrroloquinoline quinone 2,6-Lutidine 2,4,6-Collidine Pyridine sulfur trioxide

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