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
CAS Number	865-48-5 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	63267 Y
ECHA InfoCard	100.011.584
PubChem CID	70078
CompTox Dashboard (EPA)	DTXSID7073935
InChI InChI=1S/C4H9O.Na/c1-4(2,3)5;/h1-3H3;/q-1;+1 Y Key: MFRIHAYPQRLWNB-UHFFFAOYSA-N Y InChI=1/C4H9O.Na/c1-4(2,3)5;/h1-3H3;/q-1;+1 Key: MFRIHAYPQRLWNB-UHFFFAOYAB
SMILES [Na+].[O-]C(C)(C)C CC(C)(C)[O-].[Na+]
Properties
Chemical formula	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). Y verify (what is YN ?) 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 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

Related compounds

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