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 | |
| Names | |
|---|---|
| IUPAC name diethylzinc | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.008.330 |
| EC Number |
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| UNII | |
| UN number | 1366 |
| |
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| Properties | |
| Zn(CH2CH3)2 | |
| Molar mass | 123.50 g/mol |
| Appearance | colourless liquid |
| Density | 1.205 g/mL |
| Melting point | −28 °C (−18 °F; 245 K) |
| Boiling point | 117 °C (243 °F; 390 K) |
| Reacts | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Flammable and corrosive liquid, pyrophoric in air, may explode in contact with water. |
| GHS labelling: | |
   | |
| Danger | |
| H225,H250,H260,H302+H312+H332,H314,H410 | |
| P210,P222,P223,P231+P232,P233,P240,P241,P242,P243,P260,P264,P273,P280,P301+P330+P331,P302+P334,P303+P361+P353,P304+P340,P305+P351+P338,P310,P321,P335+P334,P363,P370+P378,P391,P402+P404,P403+P235,P405,P422,P501 | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related compounds | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Diethylzinc, orDEZ, is anorganozinc compound with thechemical formulaZn(CH2CH3)2. It is highlypyrophoric and reactive, consisting of azinc center bound to twoethyl groups. This colourless liquid is an importantreagent inorganic chemistry. It is available commercially as a solution inhexanes,heptane, ortoluene, or as a pure liquid.
Edward Frankland first reported the compound in 1848 from zinc andethyl iodide, the first organozinc compound discovered.[2][3] He improved the synthesis by usingdiethyl mercury as starting material.[4] The contemporary synthesis consists of the reaction of a 1:1 mixture of ethyl iodide and ethyl bromide with azinc-copper couple, a source of reactive zinc.[5]
The compound crystallizes in atetragonal body-centeredunit cell ofspace group symmetry I41md. In thesolid-state diethylzinc shows nearly linear Zn centres. The Zn-C bonds measure 194.8(5) pm, while the C-Zn-C angle is slightly bent with 176.2(4)°.[6] The structure of thegas-phase shows a very similar Zn-C distance (195.0(2) pm).[7]
Despite its highly pyrophoric nature, diethylzinc is an important chemical reagent. It is used inorganic synthesis as a source of the ethylcarbanion inaddition reactions tocarbonyl groups. For example, theasymmetric addition of anethyl group tobenzaldehyde[8] andimines.[9]Additionally, it is commonly used in combination withdiiodomethane as aSimmons-Smith reagent to convertalkenes intocyclopropyl groups.[10][11] It is lessnucleophilic than relatedalkyllithium andGrignard reagents, so it may be used when a "softer" nucleophile is needed.It is also used extensively inmaterials science chemistry as a zinc source in the synthesis ofnanoparticles. Particularly in the formation of thezinc sulfide shell for core/shell-typequantum dots.[12]While inpolymer chemistry, it can be used as part of the catalyst for achain shuttling polymerization reaction, whereby it participates in living polymerization.[13]
Diethylzinc is not limited to only being used in chemistry. Because of its high reactivity toward air, it was used in small quantities as ahypergolic or "self igniting" liquid rocket fuel[14]: 9 [15]: 323 —it ignites on contact with oxidizer, so the rocket motor need only contain a pump, without a spark source for ignition. Diethylzinc was also investigated by the United StatesLibrary of Congress as a potential means ofmass deacidification of books printed on wood pulp paper. Diethylzinc vapour would, in theory, neutralize acid residues in the paper, leaving slightlyalkalinezinc oxide residues. Although initial results were promising, the project was abandoned. A variety of adverse results prevented the method's adoption. Most infamously, the final prototype suffered damage in a series of diethylzinc explosions from trace amounts of water vapor in the chamber. This led the authors of the study to humorously comment:
It has also been established that tight or loose packing of books; the amount of alkaline reserve; reactions of DEZ with degradation products, unknown paper chemicals and adhesives; phases of the moon and the positions of various planets and constellations do not have any influence on the observed adverse effects of DEZ treatment.[16]
In microelectronics, diethylzinc is used as adoping agent.[citation needed]
For corrosion protection innuclear reactors of thelight water reactor design,depleted zinc oxide is produced by first passing diethylzinc through anenrichment centrifuge.
The pyrophoricity of diethylzinc can be used to test the inert atmosphere inside aglovebox. An oxygen concentration of only a few parts per million will cause a bottle of diethylzinc to fume when opened.[17]
Diethylzinc may explode when mixed with water and can spontaneouslyignite upon contact with air. It should therefore be handled usingair-free techniques.
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