Sodium 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

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.

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]

References

1. Dewick, Paul M. (2013-03-20). Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. John Wiley & Sons. ISBN   978-1-118-68196-1.
2. http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=359270%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC ^{[ permanent dead link ‍]}
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. Broderick, Erin M.; Browne, Samuel C.; Johnson, Marc J. A. (2014). "Dimolybdenum and Ditungsten Hexa(Alkoxides)". Inorganic Syntheses: Volume 36. Vol. 36. pp. 95–102. doi:10.1002/9781118744994.ch18. ISBN   978-1-118-74499-4.
6. 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 (44): 16666–16672. doi: 10.1039/C4DT01930J . hdl: 10852/55422 . PMID   25265332.
7. 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.
8. Bennett, Chad E. (2008). "Sodium tert -Amyloxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01008. ISBN   978-0-471-93623-7.