Organometallic Specialties

Albemarle started producing alkali alkoxides in the early 1970s and has been continuously expanding the product line ever since.

Today organolithium amides are indispensable tools in modern, selective organic synthesis. These bases are typically used for the formation of enolates. Another important application is the ortho-selective deprotonation of aromatic substrates. Albemarle offers a great variety of different amides. These reagents include amides such as LiNH₂, lithium diisopropylamide (LDA), and lithium hexamethyldisilazide (LHMDS, LHS).

Lithium Amides

Albemarle provides lithium amides starting with lithium amide (LiNH₂) up to hindered amides such as lithium diisopropylamides (LDA), and lithium hexamethyldisilazide (LHMDS, LHS). Organolithium amides are indispensable tools in modern, selective organic synthesis. These bases are typically used for the formation of enolates. Another important application is the ortho-selective deprotonation of aromatic substrates.

Butyllithium, Hexyllithium

The most commonly used reagents are butyllithium and hexyllithium. They are available on a large industrial scale. These reagents can be used as strong bases in deprotonation reactions or for halogen/metal-exchange reactions. The use of hexyllithium as a base avoids the emission of butane.

Other Lithium Organics

Special organolithium compounds like methyllithium, phenyllithium and lithium acetylide-ethylene diamine are also available in multi-tons production quantities. Phenyllithium can be used either as a base but also - like the methyllithium and the lithium acetylide ethylene diamine complex - for the introduction of the respective organic group.

• Methyllithium
• Phenyllithium
• tert-butyllithium
• Lithium acetylide

Experience and History

Albemarle is one of the world's leading manufacturers of lithium-based compounds and an innovative developer of metal-based fine chemicals for specialty applications. For many years now, organolithium compounds have been straightforward reagents for organic syntheses. In the 1960s butyllithium, as one of the most prominent products in this group, started its industrial career as an initiator of the anionic polymerization of alkenes in the synthetic rubber industry. Some decades later, pharmaceutical companies discovered the properties of butyllithium for their own syntheses, which allows for these versatile reagents to be used in the metalation of organic substrates. More and more companies are now equipped to use butyllithium and other organolithium compounds, which increases their technical capabilities of doing organic syntheses.

Grignard Compounds / Organomagnesium Compounds

Dibutylmagnesium

Dibutylmagnesium is used as a metalating agent for amines, alcohols, and carboxylic acids as well as a reagent for the synthesis of Ziegler-Natta catalyst systems and a modifier of anionic polymerization initiation. While already offering a wide range of products, Albemarle is also constantly developing new and innovative ones. Most importantly, Albemarle is able to support the specific, unique needs of each of its customers because of its extensive knowledge and experience in the areas of organolithium and organomagnesium chemistry. This experience includes both industrial and laboratory scale applications.

Grignards

Purchasing ready-made Grignard solutions instead of producing them in-house helps avoid the well-known potential hazard of the Grignard formation reaction (accumulation, sudden start of reaction, high evolution of heat) and the handling of occasionally highly toxic halogenated hydrocarbons (e.g. methyl bromide), additionally freeing up reactor capacity for higher value products.

Our Experience - Your Advantage

We are a specialty chemicals manufacturer and recognized expert in the field of air-sensitive organometallic reagents for more than forty years, started to produce and market Grignard compounds at about 1980. Not only has it kept extending the product range ever since; recently it introduced a new class of organomagnesium compounds to perform halogen/metal exchange reactions, the TurboGrignards.

TurboGrignards

Besides C-C coupling reagents Albemarle offers a new class of organomagnesium compounds for halogen-metal exchange reactions: the TurboGrignards. A mixture of secondary alkyl-magnesium chloride with LiCl in THF combines high reactivity with high functional group-tolerance in halogen-metal exchange reactions.

Grignards in Green Solvents: 2-Methyltetrahydrofuran

Albemarle offers various organomagnesium compounds in 2-MeTHF. These solutions are typically higher concentrated compared to standard THF solutions and are even more crystallization-stable (< -10 °C).
2-MTHF provides a lot of advantages in the customer process application.

Toolbox for Organozinc Chemistry

The very useful application of organozinc reagents in C-C cross-coupling reactions was honored in 2010 by awarding the Nobel Prize to Ei-ichi Negishi, Akira Suzuki, and Richard H. Heck. The demands of today’s API and natural product synthesis require selective and reactive building blocks. The production department in any pharmaceutical or chemical company must also meet safety and environmental regulations as well as operate in a profitable manner. Organozinc reagents meet all of these requirements. In contrast to lithium and magnesium organometallics, the corresponding zinc reagents exhibit a high degree of chemo selectivity and are tolerated by a large number of functional groups. Even though organozinc reagents do not exhibit a high reactivity towards most functional groups, in the presence of transition-metal catalysts they easily undergo C-C coupling reactions with an electrophile in a Negishi protocol. The application spectrum of organozinc reagents is comparable to that of boronic acid derivatives used in Suzuki coupling protocols or organotin compounds in Stille coupling protocols.