2,6-Di-tert-butylpyridine

2,6-Di-tert-butylpyridine
IUPAC name 2,6-Di-tert-butylpyridine
Other names Dibutylpyridine
Identifiers
PubChem	68510
ChemSpider	61785 Y
Jmol-3D images	Image 1
SMILES n1c(cccc1C(C)(C)C)C(C)(C)C
InChI InChI=1S/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3 Y Key: UWKQJZCTQGMHKD-UHFFFAOYSA-N Y InChI=1/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3 Key: UWKQJZCTQGMHKD-UHFFFAOYAA
Properties
Molecular formula	C13H21N
Molar mass	191.3125
Appearance	colourless liquid
Density	0.885 g/cm3
Hazards
Flash point	72.2 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,6-Di-tert-butylpyridine is an organic compound with the formula (Me₃C)₂C₅H₃N. This colourless, oily liquid is a derived from pyridine by replacement of the two H atoms with tert-butyl groups. It is a hindered base. For example, it can be protonated, but it does not form an adduct with boron trifluoride. It is prepared by the reaction of tert-butyllithium with pyridine in a manner reminiscent of the Chichibabin reaction.^[1] Several related compounds have been described, including 2,4,6-tri-t-butylpyridine.^[2]

References

1. ^ Edward Deutsch, Nai Kong V. Cheung "Noncoordinating buffers. I. Synthesis and characterization of water soluble derivatives of 2,6-di-tert-butylpyridine" J. Org. Chem. 1973, vol 38, pp 1123–1126. doi:10.1021/jo00946a013
2. ^ Francis V. Scalzi, Norman F. Golob "Alkylation of pyridine with tert-butyllithium. Convenient syntheses of 2,6-di-tert-butylpyridine and 2,4,6-tri-tert-butylpyridine" J. Org. Chem. 1971, vol 36, pp 2541–2542 doi:10.1021/jo00816a036