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; 162.0 °F; 345.3 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.^[1] For example, it can be protonated, but it does not form an adduct with boron trifluoride.

Preparation

2,6-Di-tert-butylpyridine is prepared by the reaction of tert-butyllithium with pyridine.^[2] The synthesis is reminiscent of the Chichibabin reaction.

Some related bulky pyridine compounds have been described, including 2,4,6-tri-t-butylpyridine.^[3] and 2,6-di-tert-butyl-4-methylpyridine.^[4]

References

1. ↑ Rafael R. Kostikov, Sánchez-Sancho Francisco, María Garranzo and M. Carmen Murcia "2,6-Di-t-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2010. doi:10.1002/047084289X.rd068.pub2
2. ↑ 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
3. ↑ 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. Hongmei Li "2,4,6-Tri-tert-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2004. doi:10.1002/047084289X.rn00512
4. ↑ Alexandru T. Balaban "2,6-Di-tert-butyl-4-methylpyridine (DTBMP)" Encyclopedia of Reagents for Organic Synthesis 2004. doi:10.1002/047084289X.rn00509