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Molecular formula

This light weight aliphatic hydrocarbon belongs to the category containing cyanides and cyanohydrins, which are N-containing aliphatic organic compounds. It is also referred to as Trimethyl acetonitrile and denoted with the semi-structural formula (CH3)3CCN.

PharmaCompass offers information on [Pivalonitrile, CAS Number 630-18-2] for your research and manufacturing needs. Find product specific information including suppliers, manufacturers, chemical information CAS, MSDS, protocols and references.

Physical and Chemical Characteristics

Pivalonitrile weighs 83.13 grams per mole and exists as a clear colorless liquid that is used as a solvent and as a labile ligand in coordination chemistry. It is a polymer of tert-butyl isocyanide. It exhibits absorbance peaks at 2980 to 3000 cm-1 on Vapor Phase IR Spectra and 1.39 ppm on 1H- NMR spectra. Other spectroscopic techniques on the Pivalonitrile intermediate show the results of Total Peaks-46, m/z Top Peak-42, m/z 2nd Highest peak-41, m/z 3rd Highest peak-68 and it is considered as a highly flammable liquid at standard temperature and pressure.

The melting point of pivalonitrile is 15-16°C and the boiling point is 105-106°C.

Molecular structure
Information on Toxicity is as follows
  • H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
  • H301 (89.29%): Toxic if swallowed [Danger Acute toxicity, oral]
  • H302 (10.71%): Harmful if swallowed [Warning Acute toxicity, oral]
  • H311 (89.29%): Toxic in contact with skin [Danger Acute toxicity, dermal]
  • H315 (10.71%): Causes skin irritation [Warning Skin corrosion/irritation]
  • H319 (10.71%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
  • H331 (89.29%): Toxic if inhaled [Danger Acute toxicity, inhalation]

Currently, it is considered as a toxic chemical and should not be used without precautions.

Industrial Applications of Pivalonitrile

The physicochemical characterization and application of this methyl-based nitrile compound has been carried out through histogram analysis at Silica/Vapor, Silica/Liquid, and Liquid/Vapor Interfaces in one of the earliest research studies. Since it contains bulky tertiary butyl groups, the characterization and modifications are focused on understanding the topology and morphology of the compound at specific temperature and pH conditions. The application of pivalonitrile is through its chemical derivatives and associated alkylated salts and cationic complexes containing cyanide (-CN) groups. The chemical suppliers of TRIMETHYLACETONITRILE Intermedate are concentrated in France, Belgium, Switzerland, Ukraine, Russia, Hong, Taiwan and China. Various chemical manufacturers are considering the routes of supplying the compound in negligibly inactive form or by using commonly found precursor chemicals which are less toxic in nature. Interestingly, some researchers have discovered pathways of de novo synthesis of pyrimidine derivatives using trimethylacetonitrile through direct condensation and even delivered them to be optically active.

Chemical Synthesis Methods of Nitriles

Almost all nitriles including pivalonitrile can be manufactured industrially through Ammoxidation, Hydrocyanization, Dehydration of amides and oximes and through diazonium compounds. Even hydrolysis and reduction are viable methods to synthesize aliphatic nitriles like Pivalonitrile. Since nitriles are utilized to characterize and produce various organic solvents and polymers, they need careful consideration in case of purchase orders and bulk requirements. Nitriles are finding a place in healthcare by establishing pharmaceutical significance and tolerable biocompatibility properties. The technologies that have been patented for pivalonitrile Intermediate manufacturers include creating furo and pyrrolo analogs, inhibitory compounds against blood clotting and Tetrahydrothienopyridine derivatives – used to prevent platelet aggregation.

Published Research Work on Pivalonitrile
  1. Long bonds and short barriers: ionization and isomerization of alkyl nitriles; Mayer PM1, Guest MF, Cooper L, Shpinkova LG, Rennie EE, Holland DM, Shaw DA.

Ab initio molecular orbital calculations demonstrate that ionizing alkyl nitriles produces a dramatic geometry change involving lengthening of a C-CH(2)CN bond. The experimental determination of the adiabatic ionization energy of these species is thus very difficult. In addition, there are generally low barriers for 1,2-H shift reactions in the molecular ions leading to RCHCHN(+*) and RCHCNH(+*) isomers, which makes generating pure ionized alkyl nitrile in a mass spectrometer a challenge.

  1. Accessibility of acid sites in hierarchical zeolites: quantitative IR studies of pivalonitrile adsorption, K Sadowska, K Go?ra-Marek, J Datka - The Journal of Physical …, 2013 - ACS Publications

Accessibility studies of acid sites in zeolites involving quantitative IR measurements with hindered pivalonitrile as probe molecule were performed. The extinction coefficients of the diagnostic bands of pivalonitrile interacting with Brønsted and Lewis acid sites were

  1. The vibrational spectrum of trimethyl acetonitrile; K Kumar - Spectrochimica Acta Part A: Molecular Spectroscopy, 1972 – Elsevier

Abstract The laser-Raman spectrum of trimethyl acetonitrile in liquid state was obtained along with depolarization data, and the ir spectra were recorded both in liquid and vapour phase in the region 250–3150 cm- 1. These data were used to assign the vibrational spectrum of trimethyl acetonitrile.

  1. The Reduction of Trimethylacetonitrile with Grignard Reagents1; HS Mosher, WT Mooney - Journal of the American Chemical …, 1951 - ACS Publications

It has been shown that ethylmagnesium bromide readily adds to trimethylacetonitrile to give a good yield of the normal addition product. However, t-butylmagnesium chloride does not add normally to this hindered nitrile instead a small yield of the reduction product, trimethylacetaldehyde is formed.

  1. Structure and dynamics of trimethylacetonitrile at the silica/vapor, silica/liquid, and liquid/vapor interfaces; F Ding, CA Rivera, Q Zhong, K Manfred… - The Journal of …, 2012 - ACS Publications

Optical spectroscopy has been used to probe the interfacial organization and dynamics of trimethylacetonitrile (TMACN). Molecular orientation at the silica/liquid, silica/vapor and liquid/vapor interfaces of TMACN has been studied using vibrational sum-frequency generation (VSFG) spectroscopy.

  1. Stabilizing high-valent metal ions with a ketimide ligand set: synthesis of Mn(N=C(t)Bu2)4; Lewis RA1, Wu G, Hayton TW Inorg Chem. 2011 May 16;50(10):4660-8. doi: 10.1021/ic200490v.

Reaction of MnCl(2) with 4 equiv of Li(N=C(t)Bu(2)) generates [Li(THF)](2)[Mn(N=C(t)Bu(2))(4)] (1) in 80% yield. Oxidation of 1 with 0.5 equiv of I(2) produces [Li][Mn(N=C(t)Bu(2))(4)] (2) in 88% yield. Both complexes 1 and 2 exhibit tetrahedral structures about the Mn center in the solid-state, as determined by X-ray crystallography. Reaction of 2 with 12-crown-4 generates [Li(12-crown-4)(2)][Mn(N=C(t)Bu(2))(4)] (3) in 94% yield. Interestingly, in the solid-state, complex 3 exhibits a squashed tetrahedral structure about Mn. Addition of 1 equiv of I(2) to 1 generates the Mn(IV) ketimide, Mn(N=C(t)Bu(2))(4) (4), in 75% yield. 

  1. Chlorine derivatives of trimethyl acetonitrile OW Cass - US Patent 2,425,029, 1947 - Google Patents

This invention relates to the production of cer tain new and unique chlorinated aliphatic compounds which have a high thermal stability and a high chemical reactivity with other compounds. It is an object of this invention to produce chlorinated aliphatic compounds containing cyano groups, which compounds have a high thermal stability and in which both chlorine and cyano substituents have a high chemical reactivity.

  1. Measurement of Henry's Law Constants Using Internal Standards. A Quantitative GC Experiment for the Instrumental Analysis or Environmental Chemistry Laboratory

C Ji, SM Boisvert, AMC Arida… - Journal of chemical …, 2008 - ACS Publications

An internal standard method applicable to undergraduate instrumental analysis or environmental chemistry laboratory has been designed and tested to determine the Henry's law constants for a series of alkyl nitriles. In this method, a mixture of the analytes and an internal standard is prepared and used to make a standard solution (organic solvent) as well as a dilute aqueous solution. Both the standard solution and the headspace samples above the aqueous solution at partitioning equilibrium in closed containers are subject to gas chromatographic (GC) analysis. 

  1. Octa-[mu]3-selenido-penta­kis­(tri­ethyl­phos­phane-[kappa]P)(tri­methyl­aceto­nitrile-[kappa]N)-octa­hedro-hexa­rhenium(III) bis­(hexa­fluorido­anti­monate) tri­methyl­aceto­nitrile monosolvate YX Ren, AM Bruck, LF Szczepura - Acta Crystallographica Section E …, 2014 -

The crystal structure of the title compound, [Re6Se8{NCC(CH3)3}(Et3P)5](SbF6)2·NCC(CH3)3, contains a face-capped octa­hedral [Re6(3-Se)8]2+ cluster core. The pseudo-centrosymmetric [Re6Se8]2+ cluster core is bonded through the Re atoms to five tri­ethyl­phosphane ligands and one tri­methyl­aceto­nitrile ligand. No significant interactions are observed between the cationic cluster, the SbF6- anions and the trimethylacetonitrile solvent molecule.

  1. Synthesis of pyrimidines by direct condensation of amides and nitriles; M Movassaghi, MD Hill - Nature protocols, 2007 -

A protocol for the single-step synthesis of pyrimidine derivatives by condensation of N-vinyl or N-aryl amides with nitriles is described. Gram-scale synthesis of 4-tert-butyl-2-phenyl-7,8-dihydro-6H-pyrano[3,2-d]pyrimidine serves as a representative procedure for this methodology for azaheterocycle synthesis. This chemistry involves amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine and the necessary nitrile. Nucleophilic addition of the nitrile to an activated intermediate followed by annulation affords the pyrimidine product in a single step. The total time necessary for the completion of this procedure is approximately 3 h. This chemistry has been applied to a wide range of amides and nitriles including optically active derivatives.