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N-Butyllithium

Chemical Formula: C4H9Li
CAS: 109-72-8

N-Butyllithium (BuLi) is a highly reactive, pale yellow organolithium reagent, belonging to the class of strongly basic and strongly nucleophilic compounds. It is usually supplied in the form of alkane solutions (such as hexane or cyclohexane). It plays a crucial role in organometallic synthesis, polymerization catalysis, fine chemicals, and the preparation of pharmaceutical intermediates, and is recognized as an irreplaceable and essential basic reagent in the field of organic synthesis, possessing extremely high reactivity and strong basicity.
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N-Butyllithium Basic Properties

  • Molecular Formula: C4H9Li

  • Appearance: Yellow liquid

  • Molecular Weight: 64.06

  • Melting Point: -95 °C

  • Boiling Point: 80 °C

  • Density: 0.68 g/mL at 20 °C

  • Vapor Pressure: 163 hPa ( 20 °C)

  • Flash Point: 10 °F

  • Storage Conditions: 2-8°C

  • Solubility: Miscible with diethyl ether and cyclohexane

  • Package Information: 100g, 500g, 1kg, or customized

N-Butyllithium Key Features

High reactivity

Under strictly controlled conditions, N-Butyllithium can achieve highly selective reactions, such as preferential deprotonation reactions rather than addition to intramolecular electrophilic centers.

Extremely strong base

This compound is an extremely strong base and nucleophile with an extremely high pKa, enabling it to perform a variety of deprotonation reactions that cannot be accomplished by conventional bases. It has irreplaceable value in the construction of complex organic structures.

Excellent reaction versatility

N-Butyllithium can also undergo lithium-halogen exchange reactions and lithium-metal transfer metallization reactions (such as organotin).

Diverse concentrations

It offers flexible supply options, allowing for the selection of systems such as hexane, pentane, and cyclohexane to suit the application, making it more suitable for large-scale plant operations and precise laboratory control needs.

N-Butyllithium Main Applications

Organic synthesis

N-Butyllithium can be used for the deprotonation of a variety of substrates, and is particularly suitable for generating high-energy intermediates such as enol lithium, aryl lithium, and alkynyl lithium, which is a key reaction step in the construction of drug molecules.

Advanced materials

It is also used to prepare various organometallic compounds, as well as to synthesize oligomers and dendritic macromolecules with specific structures for research and application.

Fine chemicals

C4H9Li is widely used in a variety of products, including pharmaceutical intermediates, fragrances, and electronic chemical precursors, due to its high selectivity, which can effectively reduce the generation of by-products and improve product purity.

Precautions

  1. It must be stored in a cool, dry, well-ventilated area away from fire and heat sources. The packaging must be absolutely sealed and stored at a low temperature of 2-8℃.

  2. All operations involving N-Butyllithium must be performed under the protection of an inert gas (nitrogen or argon), and the operating environment must be absolutely anhydrous.

  3. Due to its extremely high activity, it must be handled using a completely dry metal syringe or the Schlenk system.

  4. Open flames are strictly prohibited in the workplace. Dry sand or Class D dry powder fire extinguishers should be readily available within easy reach. Never use water, foam, or chloroalkane fire extinguishers to extinguish N-Butyllithium fires.

  5. Do not operate under normal ventilation conditions. Experiments or dispensing operations should be carried out in a dedicated fume hood, drying box, or glove box to ensure safety.

  6. Waste liquid cannot be discharged directly and must be treated in accordance with hazardous chemical standards. It must be treated by professionals using a slow quenching method to avoid accidents caused by uncontrolled reactions.

FAQ

1. What is N-Butyllithium? How does it differ from other organolithium compounds?

N-Butyllithium, with the chemical formula C4H9Li, is one of the most commonly used and important organolithium reagents, exhibiting strong base and strong nucleophilicity. Compared to sec-BuLi or t-BuLi, its reactivity is slightly weaker but more controllable, making it suitable for a wider range of industrial and laboratory applications. It is typically used in alkane solution form, and due to its extreme sensitivity to air and water, it requires careful handling.


2. How to properly handle N-Butyllithium in the laboratory?

A dry glass syringe must be used under positive pressure with an inert gas atmosphere. First, flush the syringe with inert gas to displace the air, then draw the required amount from the reagent bottle under the protective atmosphere. During drawing and transfer, the needle tip should always be kept under an inert atmosphere or below the liquid surface to prevent spontaneous combustion upon contact with air. After use, the syringe should be immediately cleaned with a dry, inert solvent.


3. What are the common concentrations of C4H9Li solutions?

We typically supply concentrations of 1.6M, 2.0M, 2.5M, and 2.6M (hexane or pentane systems), and can customize solutions according to user process requirements.


4. Can it be operated in an open container for a short period of time?

No, even contact with a small amount of air will cause rapid oxidation or even spontaneous combustion. Operation must be carried out under the protection of an inert gas.


We are a professional N-Butyllithium supplier. For more information or to purchase N-Butyllithium(C4H9Li), please feel free to contact us via jomin@wolfabio.com.

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