Pivalonitrile

Last updated
Pivalonitrile
Pivalonitrile-2D-skeletal.png
Pivalonitrile-3D-balls.png
Pivalonitrile-sample.jpg
Names
Preferred IUPAC name
2,2-Dimethylpropanenitrile [1]
Other names
  • tert-Butyl cyanide
  • tert-Cyanobutane
  • 2-Cyano-2-methylpropane
  • Trimethylacetonitrile
  • tert-Butylnitrile
[2]
Identifiers
3D model (JSmol)
1361449
ChemSpider
ECHA InfoCard 100.010.122 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-133-0
PubChem CID
UNII
UN number 3273
  • InChI=1S/C5H9N/c1-5(2,3)4-6/h1-3H3 Yes check.svgY
    Key: JAMNHZBIQDNHMM-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)C#N
Properties
C5H9N
Molar mass 83.134 g·mol−1
AppearanceColourless liquid
Density 752 mg mL−1
Melting point 15 °C (59 °F; 288 K)
Boiling point 106 °C (223 °F; 379 K)
1.3774
Thermochemistry
179.37 J K−1 mol−1
232.00 J K−1 mol−1
−39.9 kJ mol−1
−3.2146–−3.2132 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg
Danger
H225, H301, H311, H331
P210, P261, P280, P301+P310, P311
Flash point 4 °C (39 °F; 277 K)
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [3]

Related Research Articles

Tetrahedrane Hypothetical organic molecule with a tetrahedral structure

Tetrahedrane is a hypothetical platonic hydrocarbon with chemical formula C4H4 and a tetrahedral structure. The molecule would be subject to considerable angle strain and has not been synthesized as of 2021. However, a number of derivatives have been prepared. In a more general sense, the term tetrahedranes is used to describe a class of molecules and ions with related structure, e.g. white phosphorus.

An isocyanide is an organic compound with the functional group -N≡C. It is the isomer of the related nitrile (-C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.

Trimethylsilyl

A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.

Bamford–Stevens reaction

The Bamford–Stevens reaction is a chemical reaction whereby treatment of tosylhydrazones with strong base gives alkenes. It is named for the British chemist William Randall Bamford and the Scottish chemist Thomas Stevens Stevens (1900–2000). The usage of aprotic solvents gives predominantly Z-alkenes, while protic solvent gives a mixture of E- and Z-alkenes. As an alkene-generating transformation, the Bamford–Stevens reaction has broad utility in synthetic methodology and complex molecule synthesis.

Trimethylsilyldiazomethane Chemical compound

Trimethylsilyldiazomethane is the organosilicon compound with the formula (CH3)3SiCHN2. It is classified as a diazo compound. Trimethylsilyldiazomethane is a commercially available reagent used in organic chemistry as a methylating agent and as a source of CH2 group. Its behavior is akin to the less convenient reagent diazomethane.

Organosilicon compound Organometallic compound containing carbon–silicon bonds

Organosilicon compounds are organometallic compounds containing carbon–silicon bonds. Organosilicon chemistry is the corresponding science of their preparation and properties. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, flammable, hydrophobic, and stable to air. Silicon carbide is an inorganic compound.

Trimethylsilyl cyanide Chemical compound

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:

Bis(trimethylsilyl)mercury Chemical compound

Bis(trimethylsilyl)mercury is a chemical reagent with the formula (CH3)3-Si-Hg-Si-(CH3)3.

TosMIC Chemical compound

TosMIC (toluenesulfonylmethyl isocyanide) is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups. It is a colourless solid that, unlike many isocyanides, is odorless. It is prepared by dehydration of the related formamide derivative. It is used in the Van Leusen reaction which is used to convert aldehydes to nitriles or in the preparation of oxazoles and imidazoles. The versatility of TosMIC in organic synthesis has been documented. It is a fairly strong carbon acid, with an estimated pKa of 14 (compared to 29 for methyl tolyl sulfone), the isocyano group acting as an electron acceptor of strength comparable to an ester group.

Lithium bis(trimethylsilyl)amide Chemical compound

Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si 3)2. It is commonly abbreviated as LiHMDS or Li(HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.

Potassium bis(trimethylsilyl)amide Chemical compound

Potassium bis(trimethylsilyl)amide (commonly abbreviated as KHMDS, Potassium(K) HexaMethylDiSilazide) is the chemical compound with the formula ((CH3)3Si)2NK. It is a strong, non-nucleophilic base with an approximate pKa of 26 (compare to lithium diisopropylamide, at 36).

Hydrogen isocyanide is a chemical with the molecular formula HNC. It is a minor tautomer of hydrogen cyanide (HCN). Its importance in the field of astrochemistry is linked to its ubiquity in the interstellar medium.

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.

Methylidynephosphane (phosphaethyne) is a chemical compound which was the first phosphaalkyne compound discovered, containing the unusual C≡P carbon-phosphorus triple bond.

Silylation is the introduction of one or more (usually) substituted silyl groups (R3Si) to a molecule. The process is the basis of organosilicon chemistry.

Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity.

Metal bis(trimethylsilyl)amides

Metal bis(trimethylsilyl)amides are coordination complexes composed of a cationic metal with anionic bis(trimethylsilyl)amide ligands and are part of a broader category of metal amides.

Trimethylsilyl iodide Chemical compound

Trimethylsilyl iodide (iodotrimethylsilane or TMSI) is an organosilicon compound with the chemical formula (CH3)3SiI. It is a colorless, volatile liquid at room temperature.

Tris(trimethylsilyl)phosphine Chemical compound

Tris(trimethylsilyl)phosphine is the organophosphorus compound with the formula P(SiMe3)3 (Me = methyl). It is a colorless liquid that ignites in air and hydrolyses readily.

Transition metal isocyanide complexes

Transition metal isocyanide complexes are coordination compounds containing isocyanide ligands. Because isocyanide are relatively basic, but also good pi-acceptors, a wide range of complexes are known. Some isocyanide complexes are used in medical imaging.

References

  1. "Pivalonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 June 2012.
  2. "Pivalonitrile | C5H9N | ChemSpider". www.chemspider.com. Retrieved 19 August 2022.
  3. Booth, M. R.; Frankiss, S. G. (1968). "Trimethylsilyl isocyanide". Chem. Commun. (21): 1347–1348. doi:10.1039/C19680001347.