What Is Diethylzinc?
Diethylzinc is an organic compound with the chemical formula (C2H5)2Zn. It is a colorless liquid at room temperature, but is often sold as a hexane solution. Its CAS registration number is 557-20-0.
Uses of Diethylzinc
Diethylzinc is used as a high-energy fuel and ignition agent for rockets due to its spontaneous ignition properties when exposed to air.
Synthetically, the substance is also used as an important alkylating agent. In particular, it was a commonly used organometallic compound as a nucleophile until the introduction of Grignard reagents in 1900.
Today it is also emphasized as a raw material for transparent zinc oxide films, which are used in touch panels and other liquid crystal display devices, and solar cells.
Properties of Diethylzinc
Diethylzinc has a molecular weight of 123.50, a melting point of -33.8°C, and a boiling point of 117.6°C. It is a clear, colorless liquid at room temperature. It has a characteristic odor and has a density of 1.205 g/mL. It reacts vigorously with water and is soluble in organic solvents in any proportion in aromatic hydrocarbons and aliphatic saturated hydrocarbons.
Types of Diethylzinc
Diethylzinc is commonly sold as an organometallic compound for industrial use and as a reagent product for research and development.
1. Reagent Products for Research and Development
The R&D reagent product is sold mainly as a solution of around 1.0M in n-hexane. The volume types include 100mL, 800mL, 2L, etc. The appearance is a clear, colorless liquid.
2. Industrial Chemicals
Products sold as industrial chemicals are used for synthesis reactions of bulk pharmaceuticals and intermediates, and as raw materials for electronic information materials. Some products are sold as gases.
Other Information on Diethylzinc
1. Synthesis of Diethylzinc
Diethylzinc is a compound synthesized by the reaction of a 1:1 mixture of ethyl iodide and ethyl bromide with a zinc-copper couple.
Historically, it was synthesized from zinc and ethyl iodide in the world’s first report by Edward Frankland in 1848. Later, an improved method was reported using diethylmercury as the starting material for this reaction.
2. Chemical Reaction of Diethylzinc
Diethylzinc is used as a nucleophile to introduce ethyl groups in synthetic organic chemistry. Addition reactions to carbonyl groups and imines are common.
When diiodomethane is applied, the Simmons-Smith reagent (ICH2ZnI) is formed. The Simmons-Smith reagent is the active species used in the chemical reaction to cyclopropanate alkenes.
3. Hazards of Diethylzinc
Diethylzinc is a spontaneously combustible substance at room temperature. It reacts explosively upon contact with water or alcohols, producing flammable hydrocarbons such as methane and metal hydrides.
Hazards to humans include burns to the skin, irritation of mucous membranes and eyes from the vapor, and pulmonary edema. Because of these hazards, it is necessary to avoid mixing with air, water, and alcohol, and to handle in an inert gas.
Commercially available products are often sold in solutions of hexane, heptane, or toluene.