Trimethylacetonitrile Chemical Properties

Melting point:

15-16 °C (lit.)

Boiling point:

105-106 °C (lit.)

Density 

0.752 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.377(lit.)

Flash point:

40 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

color 

Clear colorless

Water Solubility 

Miscible with ethanol, acetone and toluene. Slightly miscible with water.

BRN 

1361449

Exposure limits

NIOSH: IDLH 25 mg/m3

Dielectric constant

20.09

InChI

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

InChIKey

JAMNHZBIQDNHMM-UHFFFAOYSA-N

SMILES

C(#N)C(C)(C)C

CAS DataBase Reference

630-18-2(CAS DataBase Reference)

EPA Substance Registry System

Propanenitrile, 2,2-dimethyl- (630-18-2)

Safety Information

Hazard Codes 

F,T,Xi

Risk 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

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Trimethylacetonitrile Usage And Synthesis

Description

Trimethylacetonitrile is a colorless and transparent liquid with high polarity and solubility. Its dielectric constant varies with temperature and frequency. At room temperature, the dielectric constant of trimethylacetonitrile is approximately 37.5, which gradually decreases at high temperatures. The high dielectric constant of trimethylacetonitrile makes it widely used in the field of electrochemistry. For example, in electrochemical reactions, trimethylacetonitrile can be used as a solvent and electrolyte to improve the efficiency and rate of the reaction. At the same time, trimethylacetonitrile can also be used as a dielectric for capacitors, to store charge and energy.

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.

Application

Trimethylacetonitrile can be used:
As an intermediate compound, it is a product of benzopyrimidine in the preparation of 6-substituted phenanthridines^[1].
As a laboratory research material for the thermodynamic correlation index determination of chemistry, spectroscopic determination and reduction reaction studies with Grignard reagents^[2-4].

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.]

References

[1] JAN PAWLAS; Mikael B. A One-Pot Access to 6-Substituted Phenanthridines from Fluoroarenes and Nitriles via 1,2-Arynes[J]. Organic Letters, 2002. DOI:10.1021/ol026197c.
[2] T. MOHAMED. Computational (DFT and MP2) and spectral interpretations, normal coordinate analysis, force constants and barriers to internal rotations of Trimethylacetonitrile[J]. Journal of Theoretical & Computational Chemistry, 2016. DOI:10.1142/S0219633616500346.
[3] EDGAR F. WESTRUM JR. Aaron R. Trimethylacetonitrile. Low-temperature heat capacity, vapor pressure, and chemical thermodynamics of the crystalline, liquid, and gaseous phases[J]. The Journal of Physical Chemistry , 1967. DOI:10.1021/j100864a006.
[4] HARRY S. MOSHER; William T M. The Reduction of Trimethylacetonitrile with Grignard Reagents1[J]. Journal of the American Chemical Society, 1951. DOI:10.1021/ja01152a114.

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