Pivalonitrile

Pivalonitrile
Names
	Preferred IUPAC name 2,2-Dimethylpropanenitrile
	Other names tert-Butyl cyanide[citation needed]; tert-Cyanobutane[citation needed]; 2-Cyano-2-methylpropane[citation needed]; Trimethylacetonitrile[citation needed]; tert-Butylnitrile[citation needed];
Identifiers
CAS Number	630-18-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1361449
ChemSpider	11909 ;
ECHA InfoCard	100.010.122
EC Number	211-133-0;
PubChem CID	12416;
UN number	3273
CompTox Dashboard (EPA)	DTXSID7060887 ;
	show InChI
	show SMILES
Properties
Chemical formula	C5H9N
Molar mass	83.134 g·mol−1
Appearance	Colourless liquid
Density	752 mg mL−1
Melting point	15 °C (59 °F; 288 K)
Boiling point	106 °C (223 °F; 379 K)
Refractive index (nD)	1.3774
Thermochemistry
Heat capacity (C)	179.37 J K−1 mol−1
Std molar; entropy (So298)	232.00 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−39.9 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−3.2146–−3.2132 MJ mol−1
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H301, H311, H331
GHS precautionary statements	P210, P261, P280, P301+310, P311
Flash point	4 °C (39 °F; 277 K)
Related compounds
Related alkanenitriles	Acetonitrile; Aminoacetonitrile; Glycolonitrile; Cyanogen; Propanenitrile; Aminopropionitrile; Malononitrile; Acetone cyanohydrin; Butyronitrile; Succinonitrile; Tetramethylsuccinonitrile;
Related compounds	DBNPA
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

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. ^[2]

References[]

^ "Pivalonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 June 2012.
^ Booth, M. R.; Frankiss, S. G. (1968). "Trimethylsilyl isocyanide". Chem. Commun. (21): 1347–1348. doi:10.1039/C19680001347.

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[1] "Pivalonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 June 2012.

[2] Booth, M. R.; Frankiss, S. G. (1968). "Trimethylsilyl isocyanide". Chem. Commun. (21): 1347–1348. doi:10.1039/C19680001347.

[1]

[2]

Names



Preferred IUPAC name 2,2-Dimethylpropanenitrile^[1]
Other names tert-Butyl cyanide^{[citation needed]} tert-Cyanobutane^{[citation needed]} 2-Cyano-2-methylpropane^{[citation needed]} Trimethylacetonitrile^{[citation needed]} tert-Butylnitrile^{[citation needed]}
Identifiers
CAS Number	630-18-2^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1361449
ChemSpider	11909^Y
ECHA InfoCard	100.010.122
EC Number	211-133-0
PubChem CID	12416
UN number	3273
CompTox Dashboard (EPA)	DTXSID7060887
show InChI InChI=1S/C5H9N/c1-5(2,3)4-6/h1-3H3^Y Key: JAMNHZBIQDNHMM-UHFFFAOYSA-N^Y
show SMILES CC(C)(C)C#N
Properties
Chemical formula	C₅H₉N
Molar mass	83.134 g·mol⁻¹
Appearance	Colourless liquid
Density	752 mg mL⁻¹
Melting point	15 °C (59 °F; 288 K)
Boiling point	106 °C (223 °F; 379 K)
Refractive index (n_D)	1.3774
Thermochemistry
Heat capacity (C)	179.37 J K⁻¹ mol⁻¹
Std molar entropy (S^o₂₉₈)	232.00 J K⁻¹ mol⁻¹
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−39.9 kJ mol⁻¹
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	−3.2146–−3.2132 MJ mol⁻¹
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H301, H311, H331
GHS precautionary statements	P210, P261, P280, P301+310, P311
Flash point	4 °C (39 °F; 277 K)
Related compounds
Related alkanenitriles	Acetonitrile Aminoacetonitrile Glycolonitrile Cyanogen Propanenitrile Aminopropionitrile Malononitrile Acetone cyanohydrin Butyronitrile Succinonitrile Tetramethylsuccinonitrile
Related compounds	DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references