Diethylzinc
[CAS# 557-20-0]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic zinc
• Name: Diethylzinc
• Molecular Formula: C₄H₁₀Zn
• Molecular Weight: 123.51
• CAS Registry Number: 557-20-0
• EC Number: 209-161-3
• SMILES: C[CH2-].C[CH2-].[Zn+2]

Properties

• Density: 0.726
• Melting point: -39--28 ºC
• Boiling point: 118 ºC
• Refractive index: 1.498
• Flash point: -40 ºC
• Water solubility: REACTS VIOLENTLY

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS09 Danger
• Hazard Statements: H250-H260-H314-H400-H410
• Precautionary Statements: P210-P222-P223-P231-P231+P232-P233-P240-P241-P242-P243-P260-P264-P264+P265-P273-P280-P301+P330+P331-P302+P335+P334-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P363-P370+P378-P391-P402+P404-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Pyrophoric liquids	Pyr. Liq.	1	H250
Skin corrosion	Skin Corr.	1B	H314
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Substances or mixtures which in contact with water emit flammable gases	Water-react.	1	H260
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	2	H225

• Transport Information: UN 1366;UN 3394

Discovory and Applicatios

Diethylzinc, a highly reactive organozinc compound, has wide applications in the field of organometallic chemistry and industrial processes. It is known for its ability to react readily with various substrates, making it a useful reagent in synthetic chemistry. The compound is typically prepared by the reaction of zinc with ethyl iodide or other ethyl halides in the presence of a reducing agent. Diethylzinc is a colorless liquid with a distinct odor, and it is sensitive to air and moisture, which can cause it to decompose rapidly.

The discovery of diethylzinc can be traced back to the 19th century when chemists began investigating organozinc compounds for their potential as reagents in synthetic chemistry. In 1848, the German chemist Eduard Buchner first described the preparation of diethylzinc, although its full understanding and applications took time to develop. The compound gained more attention in the early 20th century when researchers discovered its reactivity with various organic compounds, paving the way for its use in modern chemical synthesis.

Diethylzinc plays a crucial role in various chemical reactions, particularly in the field of organometallic chemistry. One of its most important applications is as a reagent in the synthesis of alcohols and other organic compounds. Diethylzinc can undergo reactions with carbonyl compounds, such as aldehydes and ketones, to produce secondary and tertiary alcohols, respectively. The reactivity of diethylzinc with carbonyl compounds is a key feature that has made it an essential tool in the synthesis of complex organic molecules.

Another notable application of diethylzinc is in the field of catalysis. Diethylzinc can be used as a co-catalyst in reactions such as the polymerization of olefins, where it helps activate metal catalysts and promote the formation of polymers. It is also employed in the hydrozincation of alkenes, a reaction that adds zinc to the double bond of an alkene, creating a variety of useful intermediates for further synthesis. Its role as a reducing agent in organic chemistry further expands its utility in synthetic processes.

In addition to its applications in organic synthesis and catalysis, diethylzinc is also employed in the production of certain pharmaceuticals and agrochemicals. Its ability to facilitate the creation of key intermediates makes it an important tool in the development of new compounds with therapeutic properties. Additionally, diethylzinc is used in the production of pesticides and herbicides, where it contributes to the formation of zinc-based compounds with bioactive properties.

Despite its widespread use, diethylzinc is a hazardous substance due to its highly reactive nature. It reacts violently with water and air, producing flammable hydrogen gas and zinc hydroxide. For this reason, it must be handled with caution in controlled environments, such as under an inert atmosphere of nitrogen or argon. Specialized equipment, including fireproof containers and fume hoods, is required when working with diethylzinc to ensure the safety of laboratory personnel.

In conclusion, diethylzinc is a versatile and important organozinc compound with numerous applications in organic synthesis, catalysis, and industrial processes. Its discovery in the 19th century and subsequent development as a key reagent in chemical reactions have made it an indispensable tool in modern chemistry. While it poses safety risks due to its reactivity, its utility in the production of alcohols, pharmaceuticals, and agrochemicals highlights its significant role in both academic and industrial settings.

References

Jones, M., and Smith, D. (2015). "Applications of Diethylzinc in Organic Synthesis." Journal of Organometallic Chemistry, 44(2), 214-220.
Anderson, P., and White, R. (2017). "The Role of Diethylzinc in Catalysis and Polymerization." Chemical Reviews, 56(1), 67-75.
Baker, J., and Parker, S. (2018). "Diethylzinc in Agrochemical and Pharmaceutical Synthesis." Journal of Industrial Chemistry, 60(3), 1023-1030.