pivalonitrile

{{Chembox

| Watchedfields = changed

| verifiedrevid = 464208257

| ImageFile = Pivalonitrile-2D-skeletal.png

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 100

| ImageName = Skeletal formula of pivalonitrile

| ImageFile1 = Pivalonitrile-3D-balls.png

| ImageFile1_Ref = {{chemboximage|correct|??}}

| ImageSize1 = 100

| ImageName1 = Ball and stick model of pivalonitrile

| ImageFile2 = Pivalonitrile-sample.jpg

| ImageFile2_Ref = {{chemboximage|correct|??}}

| ImageName2 = Sample of pivalonitrile in a vial

| PIN = 2,2-Dimethylpropanenitrile{{Cite web|title=Pivalonitrile - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12416&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=8 June 2012|location=USA|date=26 March 2005|at=Identification}}

| OtherNames = {{Unbulleted list|tert-Butyl cyanide|tert-Cyanobutane|2-Cyano-2-methylpropane|Trimethylacetonitrile|tert-Butylnitrile

}}{{cite web |title=Pivalonitrile {{!}} C5H9N {{!}} ChemSpider |url=https://www.chemspider.com/Chemical-Structure.11909.html |website=www.chemspider.com |access-date=19 August 2022}}

|Section1={{Chembox Identifiers

| CASNo = 630-18-2

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

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

| UNII = AQD7ZXJ3PR

| PubChem = 12416

| ChemSpiderID = 11909

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

| EINECS = 211-133-0

| UNNumber = 3273

| Beilstein = 1361449

| SMILES = CC(C)(C)C#N

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

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

| StdInChIKey = JAMNHZBIQDNHMM-UHFFFAOYSA-N

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

}}

|Section2={{Chembox Properties

| C = 5

| H = 9

| N = 1

| Appearance = Colourless liquid

| Density = 752 mg mL⁻¹

| MeltingPtC = 15

| BoilingPtC = 106

| RefractIndex = 1.3774

}}

|Section3={{Chembox Thermochemistry

| DeltaHf = −39.9 kJ mol⁻¹

| DeltaHc = −3.2146–−3.2132 MJ mol⁻¹

| Entropy = 232.00 J K⁻¹ mol⁻¹

| HeatCapacity = 179.37 J K⁻¹ mol⁻¹

}}

|Section4={{Chembox Hazards

| GHSPictograms = {{GHS flame}} {{GHS skull and crossbones}}

| GHSSignalWord = DANGER

| HPhrases = {{H-phrases|225|301|311|331}}

| PPhrases = {{P-phrases|210|261|280|301+310|311}}

| FlashPtC = 4

}}

|Section5={{Chembox Related

| OtherFunction_label = alkanenitriles

| OtherFunction = {{Unbulleted list|Acetonitrile|Aminoacetonitrile|Glycolonitrile|Cyanogen|Propanenitrile|Aminopropionitrile|Malononitrile|Acetone cyanohydrin|Butyronitrile|Succinonitrile|Tetramethylsuccinonitrile}}

| OtherCompounds = DBNPA

}}

}}

Pivalonitrile is a nitrile with the semi-structural formula (CH₃)₃CCN, abbreviated t-BuCN. This aliphatic organic compound is a clear, colourless liquid that is used as a solvent and as a labile ligand in coordination chemistry. Pivalonitrile is isomeric with tert-butyl isocyanide but the two compounds do not exist in chemical equilibrium, unlike its silicon analog trimethylsilyl cyanide. {{cite journal|first1 = M. R.|last1 = Booth|first2 = S. G.|last2 = Frankiss|title = Trimethylsilyl isocyanide|journal = Chem. Commun.|issue = 21|year = 1968|pages = 1347–1348|doi = 10.1039/C19680001347}}