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.
Names | |
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Preferred IUPAC name Sodium tert-butoxide | |
Other names
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Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.011.584 |
PubChem CID | |
CompTox Dashboard (EPA) | |
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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). |
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]
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]
hexamer | nonamer |