630-18-2

Usage

Uses

Used in Chemical Synthesis:
Trimethylacetonitrile is used as a solvent in various chemical reactions, including the reductive coupling reaction of aromatic and aliphatic ketones in the presence of titanium(II) chloride and zinc. This reaction produces the corresponding pinacols, which are valuable intermediates in the synthesis of various organic compounds.
Used in Coordination Chemistry:
Trimethylacetonitrile is used as a labile ligand in coordination chemistry, where it forms complexes with metal ions. These complexes are useful in various applications, such as catalysts in chemical reactions and as models for understanding the structure and properties of metal-containing biomolecules.
Used in Organic Synthesis:
Trimethylacetonitrile is used as an intermediate in the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its reactivity and versatility make it a valuable building block in the development of new synthetic routes and methods.

Purification Methods

Purify it by a two-stage vacuum distillation and de-gas by the freeze-pump-thaw technique. Store it under vacuum at 0o. TOXIC, use an efficient fume hood. [Beilstein 2 IV 875.]

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

Upstream product

• 375-00-8 heptafluorobutyronitrile 
• 60-29-7 diethyl ether 
• 677-22-5 tert-butylmagnesium chloride 
• 754-10-9 2,2-dimethylpropionamide 
• 140-29-4 phenylacetonitrile 
• 75-98-9 Trimethylacetic acid 
• 108-88-3 toluene 
• 74-90-8 hydrogen cyanide 
• 115-11-7 isobutene 
• 2074-87-5 carbon nitride 
• 75-28-5 Isobutane 
• 637-91-2 2,2-dimethylpropionaldehyde oxime 
• 507-20-0 tertiary butyl chloride 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 22583-66-0 1-(4-(tert-butyl)phenyl)-2,2-dimethylpropan-1-one 
• 39536-30-6 2,2-dimethyl-N-phenylpropanimidamide 
• 7397-00-4 1-(3,4-dimethylphenyl)-2,2-dimethylpropan-1-one 
• 30314-45-5 1-(4-bromophenyl)-2,2-dimethylpropan-1-one 
• 938-16-9 2,2-dimethylpropiophenone 
• 33611-54-0 2,2-dimethyl-1-phenylpropan-1-imine 
• 5813-64-9 2.2-dimethylpropylamine 
• 754-10-9 2,2-dimethylpropionamide 
• 10526-16-6 2,5-dicyano-2,5-dimethylhexane 
• 75-98-9 Trimethylacetic acid 
• 30314-44-4 2,2-dimethyl-1-(4-methylphenyl)-1-propanone 
• 72212-93-2 N-(3-tert-butyl-[1,2,4]thiadiazol-5-yl)-acetamidine 
• 68395-80-2 2-tert-butyl-5-phenyl-1,3-oxazole 
• 69143-40-4 3,3-Dimethyl-2-iminobutyl-phenylsulfon 

Relevant academic research and scientific papers

A general benzylic C-H activation and C-C coupling reaction of zirconocenes mediated by C-N bond cleavage in: tert -butylisocyanide-unusual formation of iminoacyl complexes

Reactions of the zirconocene alkyne complex [rac-(ebthi)Zr(η2-Me3SiC2SiMe3)] (rac-(ebthi) = rac-1,2-ethylene-1,1′-bis(η5-tetrahydroindenyl)) with tert-butylisocyanide and methylbenzenes were investigated. Depending on the stoichiometry, the solvent and the reaction temperature different products were obtained. Starting with the end-on coordination of the isocyanide to the zirconium centre (2), elevated reaction temperatures and an excess of tert-butylisocyanide resulted after the elimination of the alkyne in the formation of zirconocene η2-iminoacyl cyanide complexes 3a-d. These complexes are formed by coupling with a benzyl fragment through C-H bond activation of a methyl group of methylbenzene. The dimeric cyanide bridged zirconocene complex 4 is formed as a side-product of this process. The unexpected dimer and the heterometallacycles were fully characterised, including X-ray crystallography.

A NEW ROUTE TO THE 4H-1,2-OXAZETE RING SYSTEM BY THE STEREOSPECIFIC OXIDATION OF (Z)-3,3-DIMETHYL-1,1-BIS(METHYLTHIO)-2-BUTANONE OXIME

A new synthesis of a funktionalized 4H-1,2-oxazete by oxidation of α,α-bis-(alkylthio) oxime is described.

Cyclometalated Platinum(II) Complexes with Nitrile and Isocyanide Ligands: Synthesis, Structure, and Photophysical Properties

Abstract: A series of cyclometalated platinum(II) complexes with nitrile and isocyanide ligands (RCN and RNC; R = t-Bu, Bn, Ph) have been synthesized in 60–80% yields from the dimer [{Pt(ppy)Cl}2] (Hppy is 2-phenylpyridine) and the corresponding nitriles and isocyanides. The structure of the synthesized complexes was determined by mass spectrometry, IR and NMR spectroscopy, and X-ray diffraction. The contributions of different intermolecular interactions to the crystal packing were estimated by Hirshfeld surface analysis. Photophysical properties of the synthesized complexes in solution and solid state were studied.

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature

Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.

Double metal cyanides as heterogeneous Lewis acid catalysts for nitrile synthesis: Via acid-nitrile exchange reactions

A series of transition metal-based double metal cyanides (DMCs) were studied as catalysts for the synthesis of nitriles via acid-nitrile exchange reaction. The best nitrile yields were obtained with Co3[Co(CN6)]2 DMC, which proved to be a versatile, stable, reusable and highly active catalyst, exhibiting an activity comparable to that of homogeneous Lewis acid catalysts.

Chemical Vapor Deposition of Phase-Pure Uranium Dioxide Thin Films from Uranium(IV) Amidate Precursors

Homoleptic uranium(IV) amidate complexes have been synthesized and applied as single-source molecular precursors for the chemical vapor deposition of UO2 thin films. These precursors decompose by alkene elimination to give highly crystalline ph

OXIDATIVE CONVERSION OF ALIPHATIC ALDEHYDES TO NITRILES USING OXOAMMONIUM SALT

The present invention relates to an oxidative transformation method of aliphatic benzaldehydes to nitriles using NH_4OAc through oxoammonium salts. By using stoichiometric amounts of oxoammonium salts to establish optimal reaction conditions associated with the oxidative conversion of aliphatic benzaldehydes to nitriles, high yields of nitrile can be selectively obtained, and the oxoammonium salts used can be oxidized and reused in a simple method.COPYRIGHT KIPO 2020

Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.

Dehydration of Aldoximes Using PhSe(O)OH as the Pre-Catalyst in Air

PhSe(O)OH was found to be a good pre-catalyst for aldoxime dehydrations in open air. Compared with the previously reported (PhSe)2-H2O2 system, it is more stable and milder, affording broader application scopes due to a higher functional group tolerance. The control experiments for mechanism study disclosed that air was the key factor for the reaction to maintain enough concentration of PhSeOH, which should be the real catalytic species.