Diethylaluminium cyanide | |
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diethylalumanylformonitrile |
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Other names
Cyanodiethyl Aluminum |
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Identifiers | |
CAS number | 5804-85-3 |
Properties | |
Molecular formula | C4H10AlCN Et2AlCN |
Molar mass | 111.12 g/mol |
Appearance | colorless liquid |
Density | 0.864 g/cm3 at (25 °C) liquid |
Boiling point |
162 °C/0.02 mmHg (435.15 K) °F) |
Solubility in water | Benzene, Toluene, diisopropyl ether |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Diethylaluminum cyanide is the organoaluminum compound with formula ((C2H5)2AlCN)n. This compound is usually handled as a solution in toluene. This compound is a reagent for the hydrocyanation of α,β-unsaturated ketones.[1] [2] [3][4][5]
Contents |
Diethylaluminum cyanide was originally produced in 1966. It is generated by the treatment of triethylaluminum with a slight excess of hydrogen cyanide. The product is typically stored in ampoules because it is highly toxic. It dissolves in toluene, benzene, hexane and isopropyl ether. It undergoes hydrolysis readily and is not compatible with protic solvents.
Diethylaluminum cyanide has not been examined by X-ray crystallography, although other diorganoaluminum cyanides have had their crystal structures determined. Diorganylaluminum cyanides have the general formula (R2AlCN)n, and they exist as cyclic trimers (n = 3) or tetramers (n = 4). In these oligomers one finds AlCN---Al linkages.
A compound similar to diethylaluminum cyanide is bis(trimethylsilyl)methyl]aluminium cyanide, ((Me3Si)2CH)2AlCN, which has been shown crystallographically to exist as a trimer with the following structure:[6]
More recently, bis(hydrocarbyl)aluminium cyanides have been structurally characterized, such as bis(tert-butyl)aluminium cyanide, tBu2AlCN, which forms a tetramer in the crystalline phase:[7][8]
Diethylaluminum cyanide is used for hydrocyanation of α,β- unsaturated ketones. The reaction is influenced by the basicity of the solvent. This effect arises from the Lewis acidic qualities of the reagent.[9] The purpose of this reaction is to generate alkylnitriles which are precursors to amines, amides, carboxylic acids and esters.