Trimethylacetonitrile

Base Information

• Chemical Name: Trimethylacetonitrile
• CAS No.: 630-18-2
• Deprecated CAS: 1800084-88-1
• Molecular Formula: C5H9 N
• Molecular Weight: 83.1332
• Hs Code.: 29269090
• European Community (EC) Number: 211-133-0
• NSC Number: 890
• UNII: AQD7ZXJ3PR
• DSSTox Substance ID: DTXSID7060887
• Nikkaji Number: J6.890J
• Wikipedia: Pivalonitrile
• Wikidata: Q7199624
• Mol file: 630-18-2.mol

Synonyms:TRIMETHYLACETONITRILE;Pivalonitrile;630-18-2;2,2-Dimethylpropanenitrile;tert-Butyl cyanide;Propanenitrile, 2,2-dimethyl-;2,2-Dimethylpropionitrile;tert-Butylnitrile;2-Cyano-2-methylpropane;Trimethyl acetonitrile;2,2-DIMETHYLPROPANENITRIL;NSC 890;AQD7ZXJ3PR;NSC-890;EINECS 211-133-0;AI3-33242;Neopentanenitrile;NSC890;t-BuCN;MFCD00001847;UNII-AQD7ZXJ3PR;Propanenitrile,2-dimethyl-;2,2-Dimethyl-propionitrile;Trimethylacetonitrile, 98%;2,2-dimethylpropane nitrile;2,2-Dimethyl-propanenitrile;2,2,2-trimethyl acetonitrile;(CH3)3C-CN;DTXSID7060887;AKOS009145687;CS-0017904;P0463;EN300-28910;Z-1020;Q7199624;F0001-1709;Z278179882

Chemical Property of Trimethylacetonitrile

Chemical Property:

• Vapor Pressure: 29.5mmHg at 25°C
• Melting Point: 15-16 °C (lit.)
• Refractive Index: n20/D 1.377(lit.)
• Boiling Point: 105-106°C(lit.)
• Flash Point: 40°F
• Density: 0.752g/mLat 25°C(lit.)
• Storage Temp.: 2-8°C
• Water Solubility.: Miscible with ethanol, acetone and toluene. Slightly miscible with water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 83.073499291
• Heavy Atom Count: 6
• Complexity: 77.8

Purity/Quality:

99.0% min ^*data from raw suppliers

Pivalonitrile >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FT
• Hazard Codes: F,T,Xi
• Statements: 11-23/24/25-36
• Safety Statements: 16-36/37/39-45-26-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(C)(C)C#N
• 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.

Technology Process of Trimethylacetonitrile

There total 64 articles about Trimethylacetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

pivalaldehyde (630-19-3) → tert-butyl isocyanide (630-18-2)

Guidance literature:

With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1055/s-0029-1218388

Reference yield: 85.0%

pivaloyl chloride (3282-30-2) → tert-butyl isocyanide (630-18-2)

Guidance literature:

With sulfonamide; In sulfolane; at 120 ℃; for 3h;

DOI:10.1016/S0040-4039(00)87144-0

Reference yield: 85.0%

2,2-dimethylpropionamide (754-10-9) → tert-butyl isocyanide (630-18-2)

Guidance literature:

tungsten(VI) oxide; at 115 - 350 ℃; for 1.83333h; under 0.026 Torr; Pyrolysis;

DOI:10.1055/s-2007-990782

upstream raw materials:

heptafluorobutyronitrile

diethyl ether

tert-butylmagnesium chloride

2,2-dimethylpropionamide

Downstream raw materials:

1-(4-(tert-butyl)phenyl)-2,2-dimethylpropan-1-one

2,2-dimethyl-N-phenylpropanimidamide

1-(3,4-dimethylphenyl)-2,2-dimethylpropan-1-one

1-(4-bromophenyl)-2,2-dimethylpropan-1-one

Refernces

Kinetics of the 1,2-Migration of Carbon-Centered Groups in 2-Substituted 2,2-Dimethylethyl Radicals

10.1021/ja00335a037

The research investigates the kinetics of 1,2-migration of carbon-centered groups in 2-substituted 2,2-dimethylethyl radicals. The purpose of the study was to understand the factors controlling the migration rates of different R groups and to compare their relative migratory aptitudes. The research concluded that migratory aptitudes increase along the series R = N=C < Me,CC=C < Ph < Me,CC=O < H2C=CH, with the preferred pre-exponential factors lying in the range 10^10.9-10^12.0 s^-1, and activation energies varying from 16.4 kcal/mol for R = N=C to 5.7 kcal/mol for R = H2C=CH. The study involved a range of chemicals, including tert-butylbenzene, di-tert-butylacetylene, di-tert-butyl ketone, pivalonitrile, and carbon tetrachloride, among others, to measure the rates of rearrangement relative to the rate of reaction with carbon tetrachloride by GC and GC/MS analyses.