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2,6-Di-tert-butylpyridine

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.

2,6-Di-tert-butylpyridine
Names
Preferred IUPAC name
2,6-Di-tert-butylpyridine
Other names
Dibutylpyridine
Identifiers
  • 585-48-8 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 61785 Y
ECHA InfoCard 100.008.690
  • 68510
UNII
  • OI9LF0H4MM Y
  • DTXSID80207217
  • 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
  • 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).
Y verify (what is YN ?)

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

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

tert, butylpyridine, organic, compound, with, formula, me3c, 2c5h3n, this, colourless, oily, liquid, derived, from, pyridine, replacement, atoms, with, tert, butyl, groups, hindered, base, example, protonated, does, form, adduct, with, boron, trifluoride, name. 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 2 6 Di tert butylpyridine NamesPreferred IUPAC name 2 6 Di tert butylpyridineOther names DibutylpyridineIdentifiersCAS Number 585 48 8 Y3D model JSmol Interactive imageChemSpider 61785 YECHA InfoCard 100 008 690PubChem CID 68510UNII OI9LF0H4MM YCompTox Dashboard EPA DTXSID80207217InChI InChI 1S C13H21N c1 12 2 3 10 8 7 9 11 14 10 13 4 5 6 h7 9H 1 6H3 YKey UWKQJZCTQGMHKD UHFFFAOYSA N YInChI 1 C13H21N c1 12 2 3 10 8 7 9 11 14 10 13 4 5 6 h7 9H 1 6H3Key UWKQJZCTQGMHKD UHFFFAOYAASMILES n1c cccc1C C C C C C C CPropertiesChemical formula C13H21NMolar mass 191 3125Appearance colourless liquidDensity 0 885 g cm3HazardsFlash 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 Y verify what is Y N Infobox referencesPreparation Edit2 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 Edit2 4 6 Tri tert butylpyrimidine a bulky base that is less expensive than the tert buytylpyridinesReferences Edit Rafael R Kostikov Sanchez Sancho Francisco Maria 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 Retrieved from https en wikipedia org w index php title 2 6 Di tert butylpyridine amp oldid 1118576768, wikipedia, wiki, book, books, library,

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