2,6-lutidine

from Wikipedia, the free encyclopedia
Structural formula
Structure of 2,6-lutidine
General
Surname 2,6-lutidine
other names

2,6-dimethylpyridine

Molecular formula C 7 H 9 N
Brief description

colorless liquid with an unpleasant odor

External identifiers / databases
CAS number 108-48-5
EC number 203-587-3
ECHA InfoCard 100.003.262
PubChem 7937
Wikidata Q209284
properties
Molar mass 107.16 g mol −1
Physical state

liquid

density

0.923 g cm −3

Melting point

−6 ° C

boiling point

144 ° C

Vapor pressure

5.5 hPa (20 ° C)

pK s value

6.60 (25 ° C)

solubility

soluble in water

Refractive index

1.4953 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 07 - Warning

Caution

H and P phrases H: 226-302-315-319
P: 210-260-302 + 352-305 + 351 + 338
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 2,6-lutidine ( 2,6-dimethylpyridine ) is an organic compound that belongs to the heterocycles (more precisely: heteroaromatics ). It consists of a pyridine ring that is substituted with two methyl groups. It belongs to the group of lutidines , a group of six constitutional isomers with the empirical formula C 7 H 9 N.

The 2,6-lutidine was isolated from coal tar and bone oil . It has a characteristic nutty odor.

The representation is analogous to the Hantzsch dihydropyridine synthesis from ethyl acetoacetate (as β-ketocarbonyl compound), formaldehyde and ammonia in a ratio of 2: 1: 1 in the presence of some diethylamine . Dipicolinic acid is formed by oxidation of the methyl groups .

In organic synthesis, the 2,6-lutidine is used as sterically hindered base , for example in the Schütting Zung of alcohols as a silyl ether .

Individual evidence

  1. ↑ a b c d e f g h i Entry on 2,6-lutidine 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. 3-210.
  4. ↑ G. Lunge, J. Rosenberg: Ueber die Lutidins des Steinkohlentheers , in: Reports of the German Chemical Society , 1887 , 20 , pp. 127-137 ( doi: 10.1002 / cber.18870200132 ).
  5. ^ A. Ladenburg, CF Roth: Studies on the commercially available picoline , in: Reports of the German Chemical Society , 1885 , 18 , pp. 47-54, here p. 51 ( doi: 10.1002 / cber.18850180110 ).
  6. ↑ Alvin Singer, SM McElvain: 2,6-Dimethylpyridine In: Organic Syntheses . 14, 1934, p. 30, doi : 10.15227 / orgsyn.014.0030 ; Coll. Vol. 2, 1943, p. 214 ( PDF ).
  7. ↑ Entry on Lutidine. In: Römpp Online . Georg Thieme Verlag, accessed on July 27, 2017.

Web links