Wikipedia

Sodium tert-butoxide

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

Sodium tert-butoxide
Names
Preferred IUPAC name
Sodium tert-butoxide
Other names
  • Sodium t-butoxide
  • Sodium t-butanolate
  • Sodium t-butylate
  • NaOtBu
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.584 Edit this at Wikidata
  • InChI=1S/C4H9O.Na/c1-4(2,3)5;/h1-3H3;/q-1;+1 checkY
    Key: MFRIHAYPQRLWNB-UHFFFAOYSA-N checkY
  • InChI=1/C4H9O.Na/c1-4(2,3)5;/h1-3H3;/q-1;+1
    Key: MFRIHAYPQRLWNB-UHFFFAOYAB
  • [Na+].[O-]C(C)(C)C
  • CC(C)(C)[O-].[Na+]
Properties
C4H9NaO
Molar mass 96.105 g·mol−1
Density 1.025 g/cm3
Acidity (pKa) 19[1]
Hazards
Flash point 14 °C (57 °F; 287 K)
Safety data sheet (SDS) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

Reactions

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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 obtained by the salt metathesis reaction from a ditungsten heptachloride:[5]

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

Structure

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

   
hexamer nonamer
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  • Potassium tert-butoxide
  • Lithium tert-butoxide
  • Sodium tert-amyloxide (NaOC(CH3)2C2H5), a highly soluble analogue of sodium tert-butoxide[8]

References

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  1. ^ Dewick, Paul M. (2013-03-20). Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. John Wiley & Sons. ISBN 978-1-118-68196-1.
  2. ^ http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=359270%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC [permanent dead link‍]
  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: Volume 36. Vol. 36. pp. 95–102. doi:10.1002/9781118744994.ch18. ISBN 978-1-118-74499-4.
  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 (44): 16666–16672. doi:10.1039/C4DT01930J. hdl:10852/55422. PMID 25265332.
  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.
  8. ^ Bennett, Chad E. (2008). "Sodium tert -Amyloxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01008. ISBN 978-0-471-93623-7.
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