Dimethyl zinc
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Dimethyl zinc | |||||||||||||||
other names |
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Molecular formula | C 2 H 6 Zn | |||||||||||||||
Brief description |
self-igniting colorless liquid |
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properties | ||||||||||||||||
Molar mass | 95.46 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.386 g cm −3 |
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Melting point |
−40 ° C |
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boiling point |
46 ° C |
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Vapor pressure |
501 hPa (25 ° C) |
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solubility |
violent reaction with water |
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safety instructions | ||||||||||||||||
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Thermodynamic properties | ||||||||||||||||
ΔH f 0 |
23.4 kJ / mol |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Dimethyl zinc is a chemical compound from the group of organic zinc compounds .
history
Dimethylzinc was first produced by Edward Frankland while working with Robert Bunsen in 1849 at the University of Marburg (while trying to generate radicals ). After heating a mixture of zinc and methyl iodide in an airtight vessel, there was a flash of flame after the seal was opened.
Extraction and presentation
Dimethyl zinc can be obtained by reacting methyl iodide with zinc , whereby zinc iodide is formed in addition to dimethyl zinc .
properties
Dimethylzinc is a self-igniting liquid which reacts violently on contact with moisture or moist air. The technical product is sold in solution in heptane or toluene .
structure
In the solid state , the connection exists in two modifications. The high temperature phase has a two-dimensional disorder, while the low temperature phase is ordered. The molecules have a linear structure; the Zn-C bond length is 1.927 (6) Å . A Zn-C distance of 193.0 (2) pm was measured in the gas phase .
use
Dimethylzinc can be used instead of the corresponding lithium or magnesium compounds in organic syntheses if the organic synthesis is to take place under relatively mild and non-basic conditions. Due to the high vapor pressure dimethylzinc is an excellent starting material for the metal organic chemical vapor deposition (engl. Metal organic chemical vapor deposition , MOCVD ) of group II-VI semiconductor layers (z. B. ZnO , ZnS , ZnSe , ZnTe ), and p- doped III V semiconductors (e.g. GaAs , InP , Al x Ga 1-x As), which have a variety of electronic and optoelectronic applications.
Individual evidence
- ↑ a b c d e f g h Entry on dimethyl zinc in the GESTIS material database of the IFA , accessed on January 8, 2020(JavaScript required) .
- ↑ Entry on Dimethylzinc in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Data sheet Dimethylzinc, 96% from AlfaAesar, accessed on January 21, 2020 ( PDF )(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.
- ↑ E. Frankland : note that metals, phosphorus, etc. contain a new series of organic body . In: Liebig's annals of chemistry and pharmacy . 71, No. 2, 1849, pp. 213-216. doi : 10.1002 / jlac.18490710206 .
- ↑ Dimethylzinc data sheet from Sigma-Aldrich , accessed on December 24, 2010 ( PDF ).
- ↑ John Bacsa, Felix Hanke, Sarah Hindley, Rajesh Odedra, George R. Darling, Anthony C. Jones and Alexander Steiner: The Solid State Structures of Dimethylzinc and Diethylzinc . In: Angewandte Chemie International Edition . 50, 2011, pp. 11685-11687. doi : 10.1002 / anie.201105099 .
- ^ A. Haaland, JC Green, GS McGrady, AJ Downs, E. Gullo, MJ Lyall, J. Timberlake, AV Tutukin, HV Volden, K.-A. Østby: The length, strength and polarity of metal – carbon bonds: dialkylzinc compounds studied by density functional theory calculations, gas electron diffraction and photoelectron spectroscopy . In: Dalton Transactions . 2003, pp. 4356-4366. doi : 10.1039 / B306840B .
- ^ AF Holleman , E. Wiberg , N. Wiberg : Textbook of Inorganic Chemistry . 101st edition. Walter de Gruyter, Berlin 1995, ISBN 3-11-012641-9 , p. 1377.
- ↑ Mohammad Afzaal, Mohammad A. Malik, Paul O'Brien: Preparation of zinc containing materials . In: New Journal of Chemistry . 31, 2007, pp. 2029-2040. doi : 10.1039 / b712235g .