Sodium tert-butoxide

Chemical compound From Wikipedia, the free encyclopedia

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.

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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
Appearance White solid
Density 1.025 g/cm3
Acidity (pKa) 19[1]
Hazards
Flash point 14 °C (57 °F; 287 K)
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
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

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

hexamernonamer

Related compounds

  • 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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