Names | |
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Preferred IUPAC name Lithium tert-butoxide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.016.011 |
EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
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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: | |
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]
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]
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]
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.
n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.
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.
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
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.
Molybdenum(V) chloride is the inorganic compound with the empirical formula MoCl5. This dark volatile solid is used in research to prepare other molybdenum compounds. It is moisture-sensitive and soluble in chlorinated solvents.
Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organmetallic group 2 compounds are rare and are typically limited to academic interests.
Molybdenum tetrachloride is the inorganic compound with the empirical formula MoCl4. The material exists as two polymorphs, both being dark-colored paramagnetic solids. These compounds are mainly of interest as precursors to other molybdenum complexes.
Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity.
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 tert-butoxide (or sodium t-butoxide) is a chemical compound with the formula (CH3)3CONa (abbr. NaOtBu). It is a strong, non-nucleophilic base. It is flammable and moisture sensitive. It is sometimes written in the chemical literature as sodium t-butoxide. It is similar in reactivity to the more common potassium tert-butoxide.
Metal bis(trimethylsilyl)amides are coordination complexes composed of a cationic metal with anionic bis(trimethylsilyl)amide ligands and are part of a broader category of metal amides.
Molybdenum(III) chloride is the inorganic compound with the formula MoCl3. It forms purple crystals.
Tungsten(IV) chloride is an inorganic compound with the formula WCl4. It is a diamagnetic black solid. The compound is of interest in research as one of a handful of binary tungsten chlorides.
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) 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.
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.
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:
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.
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.