| Identification | More | [Name]
TRIMETHYLACETONITRILE | [CAS]
630-18-2 | [Synonyms]
2,2-DIMETHYL-PROPANENITRILE
2,2-DIMETHYLPROPIONITRILE
PIVALONITRILE
TERT-BUTYL CYANIDE
TRIMETHYLACETONITRILE
(CH3)3C-CN
2,2-dimethyl-propanenitril
2,2-Dimethylpropionsαurenitril
2-Cyano-2-methylpropane
Pivalinsαurenitril
Pivalonitril
propanenitrile,2,2-dimethyl-
tert.-Butylcyanid
tert-Butylnitrile
Trimethylacetonitril
tert-Butyl cyanide~Pivalonitrile
Trimethylacetonitrile,98+%
Trimethyl acetaldehyde/pivalaldehyde
2,2-Dimethylpropiononitrile | [EINECS(EC#)]
211-133-0 | [Molecular Formula]
C5H9N | [MDL Number]
MFCD00001847 | [Molecular Weight]
83.13 | [MOL File]
630-18-2.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS LIQUID | [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.)
| [Fp ]
40 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [color ]
Clear colorless | [Water Solubility ]
Miscible with ethanol, acetone and toluene. Slightly miscible with water. | [Specific Heat Capacity]
Cp(liquid):179.4J/(g·K),at 25℃ | [BRN ]
1361449 | [Dielectric constant]
20.09 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [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 Data | Back Directory | [Symbol(GHS) ]
 
GHS02,GHS06 | [Signal word ]
Danger | [Hazard statements ]
H225-H301+H311+H331 | [Precautionary statements ]
P210-P233-P280-P301+P310-P303+P361+P353-P304+P340+P311 | [Hazard Codes ]
F,T,Xi | [Risk Statements ]
R11:Highly Flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R36:Irritating to the eyes. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S7/9:Keep container tightly closed and in a well-ventilated place . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [F ]
19 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29269090 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Flam. Liq. 2 |
| Hazard Information | Back Directory | [Description]
Trimethylacetonitrile(630-18-2) 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(630-18-2) 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(630-18-2) 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.
|
| Questions And Answer | Back Directory | [Hydrogenation of trimethylacetonitrile]
Trimethylacetonitrile is an aliphatic nitrile compound in which the α-carbon of the nitrile group lacks a hydrogen atom; it can be used in hydrogenation reactions to produce secondary and tertiary amines. The hydrogenation reaction is carried out in the liquid phase using a Pd/C catalyst, at a reaction temperature of 110 °C and a hydrogen pressure of 5 MPa. In the hydrogenation reaction of trimethylacetonitrile with lower-chain aliphatic N,N-dialkylamines (such as diethylamine), dineopentylamine (96.3 wt%) and neopen tylamine (2.8 wt%) were produced, whilst no trineopentylamine was formed.[5] |
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