2,6-Di-tert-butylpyridine

2,6-Di-*tert*-butylpyridine
Names
	Preferred IUPAC name 2,6-Di-tert-butylpyridine
	Other names Dibutylpyridine
Identifiers
CAS Number	585-48-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	61785 ;
ECHA InfoCard	100.008.690
PubChem CID	68510;
UNII	OI9LF0H4MM ;
CompTox Dashboard (EPA)	DTXSID80207217 ;
	InChI InChI=1S/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3 Key: UWKQJZCTQGMHKD-UHFFFAOYSA-N ; 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;
	SMILES n1c(cccc1C(C)(C)C)C(C)(C)C;
Properties
Chemical 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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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]

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References

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
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
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
Alexandru T. Balaban "2,6-Di-tert-butyl-4-methylpyridine (DTBMP)" Encyclopedia of Reagents for Organic Synthesis 2004. doi:10.1002/047084289X.rn00509

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[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