View text source at Wikipedia

2,6-Di-tert-butylpyridine

2,6-Di-tert-butylpyridine
Names
Preferred IUPAC name
2,6-Di-tert-butylpyridine
Other names
Dibutylpyridine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.690 Edit this at Wikidata
UNII
  • InChI=1S/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3 checkY
    Key: UWKQJZCTQGMHKD-UHFFFAOYSA-N checkY
  • 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
  • n1c(cccc1C(C)(C)C)C(C)(C)C
Properties
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2,6-Di-tert-butylpyridine is an organic compound with the formula (Me3C)2C5H3N. This colourless, oily liquid is 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

[edit]

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]

See also

[edit]

References

[edit]
  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