2,6-Di-tert-butylpyridine explained

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

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

• 2,4,6-Tri-tert-butylpyrimidine, a bulky base that is less expensive than the tert-butylpyridines

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.
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.
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 . Hongmei Li "2,4,6-Tri-tert-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2004.
4. Alexandru T. Balaban "2,6-Di-tert-butyl-4-methylpyridine (DTBMP)" Encyclopedia of Reagents for Organic Synthesis 2004.