630-18-2

Basic information

• Product Name: TRIMETHYLACETONITRILE
• Synonyms: 2,2-DIMETHYL-PROPANENITRILE;2,2-DIMETHYLPROPIONITRILE;PIVALONITRILE;TERT-BUTYL CYANIDE;TRIMETHYLACETONITRILE;(CH3)3C-CN;2,2-dimethyl-propanenitril;2,2-Dimethylpropionsαurenitril
• CAS NO: 630-18-2
• Molecular Formula: C₅H₉N
• Molecular Weight: 83.13
• EINECS: 211-133-0
• Product Categories: Small molecule;Building Blocks;C1 to C5;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 630-18-2.mol
• Article Data: 59

Chemical Properties

• Melting Point: 15-16 °C(lit.)
• Boiling Point: 105-106 °C(lit.)
• Flash Point: 40 °F
• Appearance: Clear colorless/Liquid
• Density: 0.752 g/mL at 25 °C(lit.)
• Vapor Pressure: 29.5mmHg at 25°C
• Refractive Index: n20/D 1.377(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Miscible with ethanol, acetone and toluene. Slightly miscible with water.
• BRN: 1361449
• CAS DataBase Reference: TRIMETHYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLACETONITRILE(630-18-2)
• EPA Substance Registry System: TRIMETHYLACETONITRILE(630-18-2)

Safety Data

• Hazard Codes: F,T,Xi
• Statements: 11-23/24/25-36
• Safety Statements: 16-36/37/39-45-26-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 19
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 630-18-2(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Trimethylacetonitrile used as a solvent and as a labile ligand in coordination chemistry. It is also used as an intermediate in organic synthesis. It is used in the presence of titanium(II) chloride and zinc to undergoes reductive coupling reaction of aromatic and aliphatic ketones including acyclic aliphatic ketones to give the corresponding pinacols.

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

• 754-10-9 2,2-dimethylpropionamide 
• 140-29-4 phenylacetonitrile 
• 75-98-9 Trimethylacetic acid 
• 2074-87-5 carbon nitride 
• 75-28-5 Isobutane 
• 53911-98-1 (1-tert-butyl-2,2-dimethyl-propylidene)-aminyl 
• 3282-30-2 pivaloyl chloride 
• 630-19-3 pivalaldehyde 
• 85362-72-7 N-<2-(3,4-Dimethoxyphenyl)-ethyl>-2,2-dimethylpropionsaeureimidchlorid Hydrochlorid 
• 75-05-8 acetonitrile 
• 1609-86-5 Tert-butyl isocyanate 
• 507-19-7 t-butyl bromide 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen 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 
• 4208-54-2 1-(furan-2-yl)-2,2-dimethylpropan-1-one 
• 31595-32-1 2,2-dimethyl-1-pyridin-2-yl-propan-1-one 
• 65321-29-1 2,2-dimethyl-1-(pyridin-3-yl)propan-1-one 
• 112023-00-4 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((E)-(R)-1-tert-butylcarbamoyl-3-phenyl-allyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

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.

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.

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.