Methyllithium

Methyllithium
Skeletal formula of tetrameric methyllithium with all implicit hydrogens shown
Names
IUPAC name
Methyllithium
Other names
Lithium methanide
Identifiers
3D model (JSmol)
3587162
ChEBI
ChemSpider
ECHA InfoCard 100.011.843 Edit this at Wikidata
EC Number
  • 213-026-4
288
  • InChI=1S/CH3.Li/h1H3; checkY
    Key: DVSDBMFJEQPWNO-UHFFFAOYSA-N checkY
  • [Li]C
Properties
CH3Li
Molar mass 21.98 g·mol−1
Reacts
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 pyrophoric
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
3
2
W
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyllithium is the simplest organolithium reagent, with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive towards water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.