Lithium tert-butoxide

Lithium tert-butoxide
Identifiers
CAS Number	1907-33-1;
3D model (JSmol)	Interactive image;
ChemSpider	108193;
ECHA InfoCard	100.016.011
EC Number	217-611-5;
PubChem CID	23664764;
CompTox Dashboard (EPA)	DTXSID9051828 ;
	InChI InChI=1S/C4H9O.Li/c1-4(2,3)5;/h1-3H3;/q-1;+1 Key: LZWQNOHZMQIFBX-UHFFFAOYSA-N;
	SMILES [Li+].CC(C)(C)[O-];
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H228, H251, H302, H314
Precautionary statements	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 [77 °F], 100 kPa). Infobox references

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. 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

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

Related compounds

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. Vol. 36. pp. 95–102. doi:10.1002/9781118744994.ch18. ISBN 9781118744994.

[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. 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. Vol. 36. pp. 95–102. doi:10.1002/9781118744994.ch18. ISBN 9781118744994.

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