Sodium t-Butoxide

Other Names:

Sodium tert-butoxide

Sodium 2-methylpropan-2-olate

t-BuONa

General Information:

Structure:

CAS Number: 865-48-5

Molecular Weight: 96.10 g/mol

Chemical Formula: NaOC(CH3)3

Sodium t-butoxide (t-BuONa) is a strong, non-nucleophilic base. The pKa of its conjugate acid (t-butanol) is about 17. Similar bases include potassium t-butoxide (t-BuOK) and lithium t-butoxide (t-BuOLi). Sodium t-butoxide is the preferred base over t-BuOK and t-BuOLi for palladium catalyzed Buchwald reactions.

Common Uses:

Base in palladium catalyzed Buchwald reactions

Procedure excerpt:

To a solution of the amine (2.81 g, 10 mmol) in dioxane (45 mL) was added the chloride (2.57 g, 9.55 mmol), XantPhos (231 mg, 0.40 mmol), and t-BuONa (1.44 g, 15 mmol). . . .

[full procedure]

Safety:

Sodium t-butoxide (t-BuONa) is a strong alkoxide base. It is a hygroscopic powder that should be stored and handled under an inert atmosphere.

References:

1) Patent Reference: WO2012129344, page 126, (7.3 MB)

2) Wikipedia: Sodium tert-butoxide (link)

3) www.sigmaaldrich.com: Sodium tert-butoxide (link)

4) www.alfa.com: A19942 Sodium tert-butoxide, 97% (link)