Lithium tert-butoxide
{{DISPLAYTITLE:Lithium tert-butoxide}}
{{Chembox
| Name = Lithium tert-butoxide
| ImageFile = LiOBu-t.png
| ImageSize = 133 px
| ImageAlt =
| PIN = Lithium tert-butoxide
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 1907-33-1
| PubChem = 23664764
| ChemSpiderID = 108193
| EC_number = 217-611-5
| StdInChI=1S/C4H9O.Li/c1-4(2,3)5;/h1-3H3;/q-1;+1
| StdInChIKey = LZWQNOHZMQIFBX-UHFFFAOYSA-N
| SMILES = [Li+].CC(C)(C)[O-]
}}
|Section2={{Chembox Properties
| C=4|H=9|O=1|Li=1
| MolarMass =
| Appearance = white solid
| Density = 0.918 g/cm3 (hexamer)
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|228|251|302|314}}
| PPhrases = {{P-phrases|210|235+410|240|241|260|264|270|280|301+312|301+330+331|303+361+353|304+340|305+351+338|310|321|330|363|370+378|405|407|413|420|501}}
| MainHazards = strong base
| FlashPt =
| AutoignitionPt = }}
}}
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{{cite journal |doi=10.1002/1521-3749(200209)628:9/10<2067::AID-ZAAC2067>3.0.CO;2-N|title=Kristall- und Molekülstrukturen von Lithium- und Natrium-tert-butoxid|year=2002|last1=Nekola|first1=Henning|last2=Olbrich|first2=Falk|last3=Behrens|first3=Ulrich|journal=Zeitschrift für Anorganische und Allgemeine Chemie|volume=628|issue=9–10|pages=2067–2070}} and hexameric forms have been characterized by X-ray crystallography.{{cite journal |doi=10.1021/ja038420m|title=Characterization of a Kinetically Stable, Highly Ordered, Octameric Form of Lithiumtert-Butoxide and Its Implications Regarding Aggregate Formation|year=2004|last1=Allan|first1=John F.|last2=Nassar|first2=Roger|last3=Specht|first3=Elizabeth|last4=Beatty|first4=Alicia|last5=Calin|first5=Nathalie|last6=Henderson|first6=Kenneth W.|journal=Journal of the American Chemical Society|volume=126|issue=2|pages=484–485|pmid=14719943|bibcode=2004JAChS.126..484A }}
Preparation
File:Csd code ZZZJZU01side view.png
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.{{cite journal |doi=10.15227/orgsyn.051.0096|title=Esterification Of Hindered Alcohols: tert-Butyl p-Toluate|journal=Organic Syntheses|year=1971|volume=51|page=96|first1=G. P.|last1=Crowther|first2=E. M.|last2=Kaiser|first3=R. A.|last3=Woodruff|first4=C. R.|last4=Hauser
}}
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):{{cite book |doi=10.1002/9781118744994.ch18|title=Inorganic Syntheses: Volume 36|volume=36|year=2014|last1=Broderick|first1=Erin M.|last2=Browne|first2=Samuel C.|last3=Johnson|first3=Marc J. A.|chapter=Dimolybdenum and Ditungsten Hexa(Alkoxides) |pages=95–102|isbn=9781118744994}}
:2 MoCl3(thf)3 + 6 LiOBu-t → Mo2(OBu-t)6 + 6 LiCl + 6 thf