2,6-Di-tert-butylpyridine

changed 477193227 2,6-Di-tert-butylpyridine 2,6-Di-tert-butylpyridine.svg 200px 2,6-di-tert-butylpyridine-from-xtal-2004-Mercury-3D-sf.png 2,6-Di-tert-butylpyridine Dibutylpyridine 585-48-8 correct CAS OI9LF0H4MM correct FDA 68510 UWKQJZCTQGMHKD-UHFFFAOYAA correct chemspider UWKQJZCTQGMHKD-UHFFFAOYSA-N correct chemspider 61785 1/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3 correct chemspider 1S/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3 n1c(cccc1C(C)(C)C)C(C)(C)C C13H21N 191.3125 colourless liquid 0.885 g/cm3 72.2 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.Rafael R. Kostikov, Sánchez-Sancho Francisco, María Garranzo and M. Carmen Murcia "2,6-Di-t-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2010. 10.1002/047084289X.rd068.pub2 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.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. 10.1021/jo00946a013 The synthesis is reminiscent of the Chichibabin reaction. Some related bulky pyridine compounds have been described, including 2,4,6-tri-t-butylpyridineFrancis 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 10.1021/jo00816a036. Hongmei Li "2,4,6-Tri-tert-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2004. 10.1002/047084289X.rn00512 and 2,6-di-tert-butyl-4-methylpyridine.Alexandru T. Balaban "2,6-Di-tert-butyl-4-methylpyridine (DTBMP)" Encyclopedia of Reagents for Organic Synthesis 2004. 10.1002/047084289X.rn00509 See also 2,4,6-Tri-tert-butylpyrimidine, a bulky base that is less expensive than the tert-butylpyridines References Category:Disubstituted pyridines Category:Reagents for organic chemistry Category:Non-nucleophilic bases Category:Tert-butyl compounds