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108-75-8 - 2,4,6-Collidine, 99% - 2,4,6-Trimethylpyridine - A11058 - Alfa Aesar

A11058 2,4,6-Collidine, 99%

CAS Number
108-75-8
Synonyms
2,4,6-Trimethylpyridine

Size Price ($) Quantity Availability
25ml 22.45
100ml 55.62
500ml 190.55
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2,4,6-Collidine, 99%

MDL
MFCD00006338
EINECS
203-613-3

Chemical Properties

Formula
C8H11N
Formula Weight
121.18
Melting point
-43°
Boiling Point
171-172°
Flash Point
54°(129°F)
Density
0.916
Refractive Index
1.4980
Solubility
Slightly miscible with water. Miscible with ether, methanol, acetone, chloroform, benzene, toluene and dilute acids.

Applications

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.

Notes

Incompatible with oxidizing agents and strong acids.

Literature References

Hindered base. For use in the dehydrochlorination of ɑ-chloroketones to enones, see: Org. Synth. Coll., 4, 162 (1963). For use in combination with Trifluoromethanesulfonic anhydride, A11767 for the generation of ketenimines from olefins, see N,N-Dimethyl­acetamide, A10924.

Superior base for peptide coupling reactions, causing less racemization than the more commonly used N-ethyldiisopropylamine or N-methylmorpholine: J. Org. Chem., 59, 695 (1994). For comparison with other hindered bases, see: J. Org. Chem., 61, 2460 (1996). For peptide reagents, see Appendix 6.

Solvent for various O-alkyl cleavage reaction by LiI, including hindered esters: J. Org. Chem., 28, 2184 (1963), and methyl ethers of phenols: Chem. Commun., 616 (1969).

/n

Dufour-Gallant, J.; Chatenet, D.; Lubell, W. D. De Novo Conception of Small Molecule Modulators Based on Endogenous Peptide Ligands: Pyrrolodiazepin-2-one γ-Turn Mimics That Differentially Modulate Urotensin II Receptor-Mediated Vasoconstriction ex Vivo. J. Med. Chem. 2015, 58 (11), 4624-4637.

Fujioka, H.; Matsumoto, N.; Ohta, R.; Yamakawa, M.; Shimizu, N.; Kimura, T.; Murai, K. Organic synthesis based on the Beckmann fragmentation: generation of an electrophilic salt intermediate and successive C-C bond formation using Gilman reagents. Tetrahedron Lett. 2015, 56 (21), 2656-2658.

GHS Hazard and Precautionary Statements

Hazard Statements: H311-H302-H315-H319-H335-H226

Toxic in contact with skin. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Flammable liquid and vapour.

Precautionary Statements: P210-P261-P280-P303+P361+P353-P305+P351+P338-P361-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,9718
Beilstein
107283
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
Yes
RTECS
UU0970000

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