Sodium tert-butoxide

Sodium tert-butoxide
Names
	IUPAC name Sodium 2-methylpropan-2-olate
	Other names Sodium t-butoxide; Sodium t-butanolate; Sodium t-butylate; NaOtBu;
Identifiers
CAS Number	865-48-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	63267 ;
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 Key: MFRIHAYPQRLWNB-UHFFFAOYSA-N ; 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
Density	1.025 g/cm3
Acidity (pKa)	19[1]
Hazards
Safety data sheet
Flash point	14 °C (57 °F; 287 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Sodium tert-butoxide is the chemical compound with the formula (CH₃)₃CONa.[2] It is a strong base and a non-nucleophilic base. It is flammable and moisture sensitive. It is sometimes written in chemical literature as sodium t-butoxide. It is similar in reactivity to the more common potassium tert-butoxide.

The compound can be produced by treating tert-butyl alcohol with sodium hydride.[3]

Uses

The main 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

Structure

Sodium tert-butoxide forms clusters in the solid state, both hexamers[5] and nonamers.[6]


hexamer	nonamer

Toxicity

Sodium t-butoxide is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin.

References

Dewick, Paul M. (2013-03-20). Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. ISBN 9781118681961.
http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=359270%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC}
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
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.
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: 16666–16672. doi:10.1039/C4DT01930J.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)

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[1] Dewick, Paul M. (2013-03-20). Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. ISBN 9781118681961.

[2] ttp://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=359270%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC}

[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] 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: 16666–16672. doi:10.1039/C4DT01930J.CS1 maint: uses authors parameter (link)

[6] 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.CS1 maint: uses authors parameter (link)