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Lithium tert-butoxide

In today's world, Lithium tert-butoxide has gained great relevance in various areas of daily life. Since its emergence, Lithium tert-butoxide has caught the attention of many people due to its impact and influence in different aspects. There are several factors that have contributed to its popularity, such as its importance in the work environment, its relevance in society, its impact on technology or its influence on contemporary culture. In this article, we will further explore the role Lithium tert-butoxide plays today and how it has managed to capture the interest of so many people around the world.

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Lithium tert-butoxide
Names
Preferred IUPAC name
Lithium tert-butoxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.011 Edit this at Wikidata
EC Number
  • 217-611-5
  • InChI=1S/C4H9O.Li/c1-4(2,3)5;/h1-3H3;/q-1;+1
    Key: LZWQNOHZMQIFBX-UHFFFAOYSA-N
  • .CC(C)(C)
Properties
C4H9LiO
Molar mass 80.06 g·mol−1
Appearance white solid
Density 0.918 g/cm3 (hexamer)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 strong base
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H228, H251, H302, H314
P210, P235+P410, P240, P241, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P405, P407, P413, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Lithium tert-butoxide is the metalorganic compound with the formula LiOC(CH3)3. A white solid, it is used as a strong base in organic synthesis. The compound is often depicted as a salt, and it often behaves as such, but it is not ionized in solution. Both octameric[1] and hexameric forms have been characterized by X-ray crystallography.[2]

Preparation

Structure of the Li6O6C6 core of LiOBu-t hexamer, as determined by X-ray crystallography.

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

As a strong base, lithium tert-butoxide is easily protonated.

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

  1. ^ 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.
  2. ^ 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. Bibcode:2004JAChS.126..484A. doi:10.1021/ja038420m. PMID 14719943.
  3. ^ 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.
  4. ^ 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 9781118744994.
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