Lithium tert-butoxide
| Identifiers | |
|---|---|
| ECHA InfoCard | 100.016.011 |
CompTox Dashboard (EPA)
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| Properties | |
| C4H9LiO | |
| Molar mass | 80.06 g·mol−1 |
| Appearance | white solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lithium tert-butoxide is the metalloorganic compound with the formula LiOC(CH3)3. A white solid, it is used as a strong base in organic synthesis. It exists as a tetrameric cubane-type cluster. It is often seen written in chemical literature as lithium t-butoxide. The compound is often depicted as a salt, and it often behaves as such, but it is not ionized in solution.[1][2]
Preparation
Lithium tert-butoxide is commercially available as a solution and as a solid, but it is often generated in situ for laboratory use because samples are so sensitive and older samples are often of poor quality. It can be obtained by treating tert-butanol with butyl lithium.[3]
Reactions
Lithium tert-butoxide is used to prepare other tert-butoxide compounds such as copper(I) t-butoxide and hexa(tert-butoxy)dimolybdenum(III):[4]
- 2 MoCl3(thf)3 + 6 LiOBu-t → Mo2(OBu-t)6 + 6 LiCl + 6 thf
References
- ^ Nekola, Henning; Olbrich, Falk; Behrens, Ulrich (2002). "Kristall- und Molekülstrukturen von Lithium- und Natrium-tert-butoxid". Zeitschrift für Anorganische und Allgemeine Chemie. 628 (9–10): 2067–2070. doi:10.1002/1521-3749(200209)628:9/10<2067::AID-ZAAC2067>3.0.CO;2-N.
- ^ Allan, John F.; Nassar, Roger; Specht, Elizabeth; Beatty, Alicia; Calin, Nathalie; Henderson, Kenneth W. (2004). "Characterization of a Kinetically Stable, Highly Ordered, Octameric Form of Lithiumtert-Butoxide and Its Implications Regarding Aggregate Formation". Journal of the American Chemical Society. 126 (2): 484–485. doi:10.1021/ja038420m. PMID 14719943.
- ^ Crowther, G. P.; Kaiser, E. M.; Woodruff, R. A.; Hauser, C. R. (1971). "Esterification Of Hindered Alcohols: tert-Butyl p-Toluate". Organic Syntheses. 51: 96. doi:10.15227/orgsyn.051.0096.
- ^ Broderick, Erin M.; Browne, Samuel C.; Johnson, Marc J. A. (2014). "Dimolybdenum and Ditungsten Hexa(Alkoxides)". Inorganic Syntheses. 36: 95–102. doi:10.1002/9781118744994.ch18. ISBN 9781118744994.