Dimethyl zinc

Structural formula
General
Surname	Dimethyl zinc
other names	Zinc dimethyl; DMZ;
Molecular formula	C 2 H 6 Zn
Brief description	self-igniting colorless liquid
External identifiers / databases
EC number	208-884-1
ECHA InfoCard	100.008.077
PubChem	11010
Wikidata	Q414430
properties
Molar mass	95.46 g mol −1
Physical state	liquid
density	1.386 g cm −3
Melting point	−40 ° C
boiling point	46 ° C
Vapor pressure	501 hPa (25 ° C)
solubility	violent reaction with water
safety instructions
H and P phrases	H: 250-260-314-410
	EUH: 014
	P: 301 + 330 + 331-305 + 351 + 338
Thermodynamic properties
ΔH f 0	23.4 kJ / mol
	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 .

{\ displaystyle \ mathrm {2 \ Zn + 2 \ CH_ {3} I \ longrightarrow Zn (CH_ {3}) _ {2} + ZnI_ {2}}}

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 .

[GESTIS-1] ↑ ^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) .

[CLP_100.008.077-2] 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 .

[Alfa-3] Data sheet Dimethylzinc, 96% from AlfaAesar, accessed on January 21, 2020 ( PDF )(JavaScript required) .

[CRC90_5_23-4] 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.

[5] 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 .