2- tert- butylpyridine

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

2- (1,1-dimethylethyl) pyridine

Molecular formula C 9 H 13 N
External identifiers / databases
CAS number 5944-41-2
EC number 622-325-2
ECHA InfoCard 100.151.098
PubChem 138630
Wikidata Q209485
properties
Molar mass 135.21 g mol −1
Physical state

firmly

Melting point
  • −33 ° C
  • 105 ° C (picrate salt)
boiling point

169 ° C (991 hPa )

solubility

poor in water (1.8 g l −1 at 25 ° C)

Refractive index

1.4891

safety instructions
GHS hazard labeling
no classification available
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

2- tert -Butylpyridine is an organic compound that belongs to the heterocycles (more precisely: heteroaromatic compounds ). It consists of a pyridine ring with a tert-butyl radical in the 2-position .

presentation

The compound can be prepared from pyridine by radical substitution in a Minisci reaction . For this purpose, pyridine is reacted with pivalic acid , silver nitrate and ammonium peroxodisulfate in a sulfuric acid solution. A tert- butyl radical is generated from pivalic acid , which then reacts with the pyridine ring in the 2-position with high selectivity. The product is obtained with an excellent yield of 97%.

Synthesis of 2-tert-butylpyridine

Individual evidence

  1. ↑ a b c d H. C. Brown, WA Murphey: A Convenient Synthesis of the Monoalkylpyridines; a New Prototropic Reaction of 3-Picoline , in: J. Am. Chem. Soc. , 1951 , 73 , pp. 3308-3312; doi : 10.1021 / ja01151a093 .
  2. ↑ HP Hopkins Jr., DV Jahagirdar, PS Moulik, DH Aue, HM Webb, WR Davidson, MD Pedley: Basicities of the 2-, 4-, 2,4-Di-, and 2,6-Disubstituted tert-Butyl Pyridines in the Gas Phase and Aqueous Phase: Steric Effects in the Solvation of tert-Butyl-Substituted Pyridines and Pyridinium Cations , in: J. Am. Chem. Soc , 1984 , 106 , pp. 4341-4348; doi : 10.1021 / ja00328a007 .
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. Jump up ↑ JA Joules, K. Mills: Heterocyclic Chemistry , 5th Edition, Blackwell Publishing, Chichester, 2010, ISBN 978-1-4051-9365-8 , pp. 125-141.