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Sodiumtert-butoxide

From Wikipedia, the free encyclopedia
Sodiumtert-butoxide
Names
Preferred IUPAC name
Sodiumtert-butoxide
Other names
  • Sodiumt-butoxide
  • Sodiumt-butanolate
  • Sodiumt-butylate
  • NaOtBu
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.011.584Edit 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 mass96.105 g·mol−1
AppearanceWhite solid
Density1.025 g/cm3
Acidity (pKa)19[1]
Hazards
Flash point14 °C (57 °F; 287 K)
Safety data sheet (SDS)[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Sodiumtert-butoxide (orsodiumt-butoxide) is achemical compound with theformula (CH3)3CONa (abbr.NaOtBu).[2] It is a strong,non-nucleophilicbase. It is flammable and moisture sensitive. It is sometimes written in the chemical literature as sodiumt-butoxide. It is similar in reactivity to the more commonpotassiumtert-butoxide.

The compound can be produced by treatingtert-butyl alcohol withsodium hydride.[3]

Reactions

[edit]

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

A typical Buchwald-Hartwig amination using sodium tert-butoxide
A typical Buchwald-Hartwig amination using sodium tert-butoxide

Sodium tert-butoxide is used to prepare tert-butoxide complexes. For examplehexa(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

[edit]

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

hexamernonamer

Related compounds

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References

[edit]
  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). "Sodiumtert -Amyloxide".Encyclopedia of Reagents for Organic Synthesis.doi:10.1002/047084289X.rn01008.ISBN 978-0-471-93623-7.
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