tert-Butyl isocyanide
Chemical compound / From Wikipedia, the free encyclopedia
tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.[1]
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Names | |||
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Preferred IUPAC name
2-Isocyano-2-methylpropane | |||
Other names
t-BuNC | |||
Identifiers | |||
3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.027.776 ![]() | ||
PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C5H9N | |||
Molar mass | 83.13 g/mol | ||
Appearance | Colorless liquid | ||
Density | 0.735 g/cm3, liquid | ||
Boiling point | 91 °C (196 °F; 364 K) | ||
N/A | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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tert-Butyl isocyanide is prepared by a Hofmann carbylamine reaction. In this conversion, a dichloromethane solution of tert-butylamine is treated with chloroform and aqueous sodium hydroxide in the presence of catalytic amount of the phase transfer catalyst benzyltriethylammonium chloride.[2]
- Me3CNH2 + CHCl3 + 3 NaOH → Me3CNC + 3 NaCl + 3 H2O
tert-Butyl isocyanide is isomeric with pivalonitrile, also known as tert-butyl cyanide. The difference, as with all carbylamine analogs of nitriles, is that the bond joining the CN functional group to the parent molecule is made on the nitrogen, not the carbon.