tert-Butyl isocyanide

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.

tert-Butyl isocyanide
Names
Preferred IUPAC name
2-Isocyano-2-methylpropane
Other names
t-BuNC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.776
UNII
  • InChI=1S/C5H9N/c1-5(2,3)6-4/h1-3H3 Y
    Key: FAGLEPBREOXSAC-UHFFFAOYSA-N Y
  • InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
    Key: FAGLEPBREOXSAC-UHFFFAOYAL
  • CC(C)(C)[N+]#[C-]
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).
Y verify (what is YN ?)
Infobox references

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.

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.

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