2,4,6-collidine

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Structural formula
Structure of 2,4,6-collidine
General
Surname 2,4,6-collidine
other names
  • 2,4,6-trimethylpyridine
  • sym- collidine
  • γ-collidine
Molecular formula C 8 H 11 N
Brief description

colorless liquid with a pyridine-like odor

External identifiers / databases
CAS number 108-75-8
EC number 203-613-3
ECHA InfoCard 100.003.286
PubChem 7953
Wikidata Q409155
properties
Molar mass 121.18 g mol −1
Physical state

liquid

density

0.914 g cm −3 (20 ° C)

Melting point

−43 ° C

boiling point

171-172 ° C

Vapor pressure

4 hPa (20 ° C)

pK s value

7.43 (25 ° C)

solubility

35 g l −1 (20 ° C)

Refractive index

1.4959 (25 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 06 - Toxic or very toxic

danger

H and P phrases H: 226-302-311-332-315-319-335
P: 261-280-305 + 351 + 338-312
Toxicological data

400 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

The 2,4,6-collidine ( 2,4,6-trimethylpyridine ) is an organic compound that belongs to the heterocycles (more precisely: heteroaromatics ). It consists of a pyridine ring that is substituted with three methyl groups. It belongs to the group of collidines , a group of six constitutional isomers with the empirical formula C 8 H 11 N. 2,4,6-Collidine is the best-known isomer of this group and is therefore among others. a. referred to only as collidine .

Manufacturing

The 2,4,6-collidine was isolated from bone oil in 1854 . The representation is analogous to the Hantzsch dihydropyridine synthesis from ethyl acetoacetate (as β-ketocarbonyl compound), acetaldehyde and ammonia in a ratio of 2: 1: 1.

use

By oxidizing the methyl groups with potassium permanganate , collidic acid is obtained .

2,4,6-collidine is used in organic syntheses, e.g. B. used dehydrohalogenation by binding the resulting hydrogen halides .

Individual evidence

  1. ↑ a b c d e f g h i Entry on 2,4,6-trimethylpyridine in the GESTIS substance database of the IFA , accessed on July 27, 2017(JavaScript required) .
  2. ↑ Zvi Rappoport: CRC Handbook of Tables for Organic Compound Identification , Third Edition, CRC Press, Boca Raton, Florida, 1984, ISBN 0-8493-0303-6 , p. 438.
  3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-510.
  4. ^ Collidine . In: Heinrich August Pierer , Julius Löbe (Hrsg.): Universal Lexicon of the Present and the Past . 4th edition. tape 4 . Altenburg 1858, p. 262 ( zeno.org ).
  5. ↑ Friedrich Auerbach: "About a new Collidine", in: Reports of the German Chemical Society , 1892 , 25  (2), pp. 3485-3490 ( doi : 10.1002 / cber.189202502219 ).
  6. ^ T. Laue, A. Plagens: Name and keyword reactions of organic chemistry , 5th edition, Teubner Verlag, Wiesbaden 2006, ISBN 3-8351-0091-2 , p. 172.
  7. ↑ Hong-Lin Zhu, Wei Xu, Jian-Fei Wang, Yue-Qing Zheng: Synthesis, crystal structures and properties of two supramolecular polymers constructed by lanthanide with pyridine-2,4,6-tricarboxylic acid . In: Synthetic Metals . tape 162 , no. 13-14 , 2012, pp. 1327-1334 , doi : 10.1016 / j.synthmet.2012.05.016 .
  8. ↑ Entry on Kollidin. In: Römpp Online . Georg Thieme Verlag, accessed on July 27, 2017.

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