Sodium tert-butoxide

Sodium tert-butoxide is the chemical compound with the formula (CH3)3CONa.[2] It is a strong base and a non-nucleophilic base. It is flammable and moisture sensitive. It is sometimes written in chemical literature as sodium t-butoxide. It is similar in reactivity to the more common potassium tert-butoxide.


Sodium tert-butoxide
Names
IUPAC name
Sodium 2-methylpropan-2-olate
Other names
  • Sodium t-butoxide
  • Sodium t-butanolate
  • Sodium t-butylate
  • NaOtBu
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.584
Properties
C4H9NaO
Molar mass 96.105 g·mol−1
Density 1.025 g/cm3
Acidity (pKa) 19[1]
Hazards
Safety data sheet
Flash point 14 °C (57 °F; 287 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

The compound can be produced by treating tert-butyl alcohol with sodium hydride.[3]

Reactions

One application for sodium tert-butoxide is as a non-nucleophilic base. It has been widely used in the Buchwald–Hartwig amination, as in this typical example:[4]

A typical Buchwald-Hartwig amination using sodium tert-butoxide

Sodium tert-butoxide is used to prepare tert-butoxide complexes. For example hexa(tert-butoxy)ditungsten(III) is thus converted by the salt metathesis reaction from a ditungsten heptachloride:[5]

NaW2Cl7(thf)5 + 6 NaOBu-t → W2(OBu-t)6 + 7 NaCl + 7 thf

Structure

Sodium tert-butoxide forms clusters in the solid state, both hexamers[6] and nonamers.[7]

hexamer
nonamer

References

  1. Dewick, Paul M. (2013-03-20). Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. ISBN 9781118681961.
  2. http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=359270%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC}
  3. PM. Dewick, 2013. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. John Wiley & Sons; p. 157. ISBN 978-1-118-68196-1
  4. Yang, Bryant H.; Buchwald, Stephen L. (1999). "Palladium-catalyzed amination of aryl halides and sulfonates". Journal of Organometallic Chemistry. 576 (1–2): 125–146. doi:10.1016/S0022-328X(98)01054-7.
  5. Broderick, Erin M.; Browne, Samuel C.; Johnson, Marc J. A. (2014). "Dimolybdenum and Ditungsten Hexa(Alkoxides)". Inorganic Syntheses. 36: 95–102. doi:10.1002/9781118744994.ch18. ISBN 9781118744994.
  6. E. Østreng, H. H. Sønsteby, S. Øien, O. Nilsen, H. Fjellvåg (2014). "Atomic layer deposition of sodium and potassium oxides: evaluation of precursors and deposition of thin films". Dalton Trans. 43: 16666–16672. doi:10.1039/C4DT01930J.CS1 maint: uses authors parameter (link)
  7. H. Nekola, F. Olbrich, U. Behrens (2002). "Kristall‐ und Molekülstrukturen von Lithium‐ und Natrium‐tert‐butoxid". Z. Anorg. Allg. Chem. 628 (9–10): 2067–2070. doi:10.1002/1521-3749(200209)628:9/10<2067::AID-ZAAC2067>3.0.CO;2-N.CS1 maint: uses authors parameter (link)
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