Methyllithium lithium bromide complex solution

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Catalog Number

ACMA00015523

Product Name

Methyllithium lithium bromide complex solution

Category

Salt

IUPAC Name

dilithium;carbanide;bromide

Molecular Weight

108.9g/mol

Molecular Formula

CH3BrLi2

Canonical SMILES

[Li+].[Li+].[CH3-].[Br-]

InChI

InChI=1S/CH3.BrH.2Li/h1H3;1H;;/q-1;;2*+1/p-1

InChI Key

FAMGJMYDHOESPR-UHFFFAOYSA-M

Application

The Methyllithium lithium bromide complex solution serves as an effective methylating agent, specifically utilized for the α-methylation of alkoxyaryl ketones. This solution, which combines methyllithium-a colorless to yellowish solution-and lithium bromide, is versatile due to its solubility in diethyl ether and slightly less so in tetrahydrofuran, although it is insoluble in hydrocarbon solvents. Its stability persists up to around 200°C before disproportionating. It also finds application in the asymmetric allylic alkylation of allylic electrophiles using a chiral copper catalyst, enabling the formation of C-C bonds at tertiary and quaternary stereogenic centers with high enantioselectivity. Additionally, it is used in synthesizing (?)-salsolidine through reaction with 6,7-dimethoxy-3,4-dihydroisoquinoline, facilitated by (?)-sparteine as a chiral ligand.

Complexity

Covalently-Bonded Unit Count

Exact Mass

107.97382g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

107.97382g/mol

Rotatable Bond Count

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