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Lithiumtert-butoxide

From Wikipedia, the free encyclopedia
Lithiumtert-butoxide
Names
Preferred IUPAC name
Lithiumtert-butoxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.016.011Edit 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
  • [Li+].CC(C)(C)[O-]
Properties
C4H9LiO
Molar mass80.06 g·mol−1
Appearancewhite solid
Density0.918 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Lithiumtert-butoxide is themetalorganic compound with the formula LiOC(CH3)3. A white solid, it is used as a strong base inorganic 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 byX-ray crystallography.[2]

Preparation

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Lithiumtert-butoxide is commercially available as a solution and as a solid, but it is often generatedin 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

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As a strong base, lithiumtert-butoxide is easily protonated.

Lithiumtert-butoxide is used to prepare othertert-butoxide compounds such ascopper(I) t-butoxide andhexa(tert-butoxy)dimolybdenum(III):[4]

2 MoCl3(thf)3 + 6 LiOBu-t → Mo2(OBu-t)6 + 6 LiCl + 6 thf

Related compounds

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References

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  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.
Compounds withnoble gases
Compounds withhalogens
Oxides andhydroxides
Compounds withchalcogens
Compounds withpnictogens
Compounds withgroup 14 elements
Compounds withgroup 13 elements
Compounds withtransition metals
Organic (soaps)
Other compounds
Minerals
Other Li-related
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