Tetramethylgermanium or tetramethylgermane is an organogermanium compound with the chemical formula Ge(CH3)4, often abbreviated as GeMe4, where Me stands for methyl. It is a colorless liquid. It is the simplest tetraorganogermane.
Synthesis Tetramethylgermanium can be synthesized by reaction between germanium tetrachloride and a Grignard reagent methylmagnesium chloride in diethyl ether.
GeCl4 + 4 CH3MgCl → Ge(CH3)4 + 4 MgCl2 Tetramethylgermanium can also be synthesized by reaction between germanium tetrachloride and dimethylzinc or dimethylcadmium. The latter is more easily separated from the resulting product due to its higher boiling point. The reaction proceeds almost quantitatively at room temperature.
GeCl4 + 2 Zn(CH3)2 → Ge(CH3)4 + 2 ZnCl2 Tetramethylgermanium can be also synthesized by heating germanium with methyl chloride in the presence of copper.
Ge + 4 CH3Cl + 2 Cu → Ge(CH3)4 + 2 CuCl2
Characteristics Tetramethylgermanium is a colorless oily liquid with a sweetish odor, similar to chloroform. It dissolves without decomposition in ethanol and diethyl ether. It reacts slowly with nitric acid at 0 °C.
Structure The tetramethylgermanium molecule is tetrahedral at the germanium and carbon atoms. The germanium atom is connected to four methyl groups by a single bond in a tetrahedral fashion, thus, tetramethylgermanium is a heavy analog of neopentane, where the central carbon atom is replaced by germanium.
Uses Tetramethylgermanium is useful as a NMR chemical shift reference compound and in production of thin films composed of germanium element and germanium-containing polymers using plasma polymerization technique. The colorless polymer films formed from tetramethylgermanium were investigated by elemental analysis and infrared spectroscopy. Those polymers contain −CH3, −CH2−, Ge−CH3, Ge−O−C, and Ge−O−Ge groups and germanium element. Most Ge species present at the outermost layers of the films are oxidized by air, while the Ge species at the inner layers exist as germanium element. Tetramethylgermanium can be used as a methylating agent in transmetallation reactions. The following reaction should be done below 20 °C (68 °F):
Ge(CH3)4 + GaCl3 → (CH3)3GeCl + CH3GaCl2
Safety Upon contact with eyes, tetramethylgermanium can cause serious eye damage and serious eye irritation. It is harmful in contact with skin, causing skin irritation. It is a neurotoxin. It is flammable. Its vapors may form explosive mixtures with air. Vapors of tetramethylgermanium are heavier than air and may spread along floors. While it burns, it releases toxic and irritating smoke and gases containing germanium oxides, carbon monoxide and carbon dioxide.
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