Lithium tert-butoxide

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Lithium tert-butoxide
LiOBu-t.png
Names
Preferred IUPAC name
Lithium tert-butoxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.011 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-611-5
PubChem CID
  • 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 mass 80.06 g·mol−1
Appearancewhite solid
Density 0.918 g/cm3 (hexamer)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
strong base
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
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 [77 °F], 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]

Contents

Preparation

Structure of the Li6O6C6 core of LiOBu-t hexamer, as determined by X-ray crystallography. Csd code ZZZJZU01side view.png
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

Related Research Articles

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<i>n</i>-Butyllithium Chemical compound

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Potassium <i>tert</i>-butoxide Chemical compound

Potassium tert-butoxide (or potassium t-butoxide) is a chemical compound with the formula [(CH3)3COK]n (abbr. KOtBu). This colourless solid is a strong base (pKa of conjugate acid around 17), which is useful in organic synthesis. The compound is often depicted as a salt, and it often behaves as such, but its ionization depends on the solvent.

<span class="mw-page-title-main">Trimethylsilyl chloride</span> Chemical compound

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<i>tert</i>-Butyllithium Chemical compound

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory.

<span class="mw-page-title-main">Molybdenum(V) chloride</span> Chemical compound

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<i>tert</i>-Butylthiol Chemical compound

tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

Sodium <i>tert</i>-butoxide Chemical compound

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Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.

Copper(I) <i>t</i>-butoxide Chemical compound

Copper(I) t-butoxide is an alkoxide of copper(I). It is a white sublimable solid. It is a reagent in the synthesis of other copper compounds.

<span class="mw-page-title-main">Metal–metal bond</span>

In inorganic chemistry, metal–metal bonds describe attractive interactions between metal centers. The simplest examples are found in bimetallic complexes. Metal–metal bonds can be "supported", i.e. be accompanied by one or more bridging ligands, or "unsupported". They can also vary according to bond order. The topic of metal–metal bonding is usually discussed within the framework of coordination chemistry, but the topic is related to extended metallic bonding, which describes interactions between metals in extended solids such as bulk metals and metal subhalides.

<span class="mw-page-title-main">Hexa(tert-butoxy)dimolybdenum(III)</span> Chemical compound

Hexa(tert-butoxy)dimolybdenum(III) is a coordination complex of molybdenum(III). It is one of the homoleptic alkoxides of molybdenum. An orange, air-sensitive solid, the complex has attracted academic attention as the precursor to many organomolybdenum derivatives. It an example of a charge-neutral complex featuring a molybdenum to molybdenum triple bond (Mo≡Mo), arising from the coupling of a pair of d3 metal centers. It can be prepared by a salt metathesis reaction from the THF complex of molybdenum trichloride and lithium tert-butoxide:

<span class="mw-page-title-main">Hexa(tert-butoxy)ditungsten(III)</span> Chemical compound

Hexa(tert-butoxy)ditungsten(III) is a coordination complex of tungsten(III). It is one of the homoleptic alkoxides of tungsten. A red, air-sensitive solid, the complex has attracted academic attention as the precursor to many organotungsten derivatives. It an example of a charge-neutral complex featuring a W≡W bond, arising from the coupling of a pair of d3 metal centers. It has attracted particular attention for its reactions with alkynes, leading to alkyne metathesis.

<span class="mw-page-title-main">Transition metal ether complex</span>

In chemistry, a transition metal ether complex is a coordination complex consisting of a transition metal bonded to one or more ether ligand. The inventory of complexes is extensive. Common ether ligands are diethyl ether and tetrahydrofuran. Common chelating ether ligands include the glymes, dimethoxyethane (dme) and diglyme, and the crown ethers. Being lipophilic, metal-ether complexes often exhibit solubility in organic solvents, a property of interest in synthetic chemistry. In contrast, the di-ether 1,4-dioxane is generally a bridging ligand.

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. 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.