tert-Butyl isocyanide

{{DISPLAYTITLE:tert-Butyl isocyanide}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 462756293

| ImageFileL1 = tert-butylisocyanide.png

| ImageFileR1 = Tert-Butyl-isocyanide_3d_structure.png

| Name = tert-Butyl isocyanide

| PIN = 2-Isocyano-2-methylpropane

| OtherNames = t-BuNC

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 7188-38-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 22S4Z857K3

| PubChem = 23577

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 22045

| SMILES = CC(C)(C)[N+]#[C-]

| InChI = 1/C5H9N/c1-5(2,3)6-4/h1-3H3

| InChIKey = FAGLEPBREOXSAC-UHFFFAOYAL

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C5H9N/c1-5(2,3)6-4/h1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FAGLEPBREOXSAC-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula = C₅H₉N

| MolarMass = 83.13 g/mol

| Appearance = Colorless liquid

| Density = 0.735 g/cm³, liquid

| Solubility = N/A

| MeltingPt =

| BoilingPtC = 91

}}

}}

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.{{Cite book |last=Malatesta |first=L. |title=Progress in Inorganic Chemistry |chapter-url=https://onlinelibrary.wiley.com/doi/10.1002/9780470166024.ch5 |chapter=Isocyanide Complexes of Metals |date=January 1959 |publisher=Wiley |isbn=978-0-470-17589-7 |editor-last=Cotton |editor-first=F. Albert |edition=1 |volume=1 |pages=283–379 |language=en |doi=10.1002/9780470166024.ch5}}

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.{{cite journal| author = Gokel, G.W.; Widera, R.P.; Weber, W.P. | title = Phase-transfer Hofmann carbylamine reaction: tert-butyl isocyanide| journal = Organic Syntheses| volume=55|doi=10.15227/orgsyn.055.0096| pages = 232| year = 1988 }}

: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.