Skip to Content
Merck
HomeProductsChemistry & BiochemicalsChemical SynthesisOrganolithium Reagents

Organolithium Reagents

Close-up of a bottle cap featuring a logo with an ‘M’ above a white circle, and the text “Sure|Seal™” in red around the lower edge of the circle.

Since its discovery by Schlenk and Holtz, lithiation chemistry has become a well-established technique in modern industrial synthesis. With the demand to synthesize highly complex natural products and obtain new chemical structures for probing uncharted territory in chemistry, organolithium reagents have become essential elements in the formation of known bond formations (e.g. nucleophilic addition and substitution) and the development of new technologies in organic synthesis. 

Organolithium compounds, being strong bases and nucleophiles, have gained outstanding importance as key intermediates and powerful reagents in organic synthesis. 

Read more

Selection of applications:

  • Organolithium reagents frequently participate in cross-coupling reactions.
  • The butyllithium isomers n-butyllithium, chiral sec-butyllithium, and t-butyllithium are widely used in organic synthesis respectively as polymerization initiators, a source of sec-butyl carbanions, and as a strong base in Grignard reactions.
  • Highly stereochemically-enriched organolithium compounds are versatile and sought-after synthetic intermediates in stereoselective synthesis.

Since organolithium reagents display high sensitivity to both air and moisture, we provide top-quality packaging in Sure/Seal™ bottles to prolong the lifetime of these reagents. Smaller-sized bottles require fewer needle entries to consume the reagent volume. Therefore, many of our organometallic reagents are also being transitioned into exclusive 25 mL Sure/Seal™ packaging to reduce waste and decomposition of more unstable reagents.

Explore how our organolithium reagents can make a difference in your scientific discoveries.

Related Applications
C–H Functionalization
C–H functionalization is the reliable and predictable conversion of a C–H into a C–C, C–N, C–O, or C–X bond in a selective and controlled fashion.
Cross-Coupling
Cross-coupling is a common reaction in organic chemistry for the creation of C-C, C-N, and C-O bonds with the aid of a metal catalyst.
Fluorination
Fluorination is the introduction of fluorine to a compound via electrophilic fluorination, nucleophilic fluorination, difluoromethylation, trifluoromethylation, or perfluoroalkylation.
Metathesis
Olefin metathesis involves an organic reaction that redistributes fragments of alkenes (olefins) by cleavage and transformation of carbon-carbon double bonds.
Photocatalysis
Photoredox catalysis uses visible light and photocatalysts for synthetic transformations like cross-coupling and functionalization reactions.
Organic Reaction Toolbox
An organic reaction toolbox provides structure-activity relationships for unique chemical reactions to optimally design and control small molecule synthesis.
Related Product Categories
Grignard Reagents
Our unparalleled portfolio of Grignard Reagents are used in reactions such as Grignard reaction to form a new carbon-carbon bond.
Related Services
SYNTHIA™ Retrosynthesis Software
Our custom cell culture product design experts can offer advice and support as you scale your bioprocess from clinical to commercial supply, assisting with liquid products, dry powder products, selection of raw materials, quality testing, flexible product packaging, and product documentation.
Sign In To Continue

To continue reading please sign in or create an account.

Don't Have An Account?