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| Dimethylzinc | |
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| IUPAC name | dimethylzinc |
| Identifiers | |
| CAS number | 544-97-8 |
| Properties | |
| Molecular formula | Zn(CH3)2 |
| Molar mass | 95.478 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Zinc methyl is a colorless mobile liquid Zn(CH3)2, formed by the action of methyl iodide on a zinc at elevated temperature or on zinc sodium alloy.
- 3Zn + 2CH3I → Zn(CH3)2 + ZnI2
It has a disagreeable odor, and is spontaneously flammable in air. It has been of great importance in the synthesis of organic compounds. It is soluble in alkanes and often sold as a solution in hexanes. It belongs to the large series of similar compounds such as diethylzinc.
History
This substance was first prepared by Edward Frankland during his work with Robert Bunsen in 1849 at the University of Marburg. After heating a mixture of zinc and methyl iodide in a airtight vessel a flame bursted out after the seal was broken.1 In laboratory scale the synthesis method did not change till today, except that copper or copper compounds are used to activate the zinc.
Dimethyl zinc was used for a long time to introduce methyl groups into organic molecules or to synthesis organometalic compounds containing methyl groups. The Grignard reagents, a magnesium organic compound, which is easier to handle and less imflamable substituted zinc methyl in most of the laboratory synthesis. There are, however, several reactions which proceed better or result in alternative products with the zinc organic compounds than with magnesium organic compounds.
References
- ^ E. Frankland (1849). "Notiz über eine neue Reihe organischer Körper, welche Metalle, Phosphor u. s. w. enthalten". Liebig's Annalen der Chemie und Pharmacie 71 (2): 213–216. doi:.
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