4-methylpentanonitrile - 4-metilpentanonitrilo
|Semi-developed formula||CH 3 -CH 2 ( CH 3 ) - (CH 2 ) 3 - C≡N|
|Appearance||Liquid clear colorless|
|Density||800 kg/m³; 0,8 g/cm³|
|Molar mass||97.16 g / mol|
|Melting point||−51 °C (222 K)|
|Boiling point||155 °C (428 K)|
|Vapor pressure||3,2 ± 3,0 mmHg|
|Refractive index (n D )||1,405|
|Solubility in water||3 g/L|
|Flash point||318,15 K (45 °C)|
|nitrilos|| valeronitrilo |
|dinitrilos|| adiponitrilo |
|Values in the SI and under standard conditions|
(25 ℃ and 1 atm ), unless otherwise indicated.
Physical and chemical properties
At room temperature, 4-methylpentanenitrile is a liquid clear and colorless having its boiling point to 155 ° C , while the melting point is -51 ° C. It has a density lower than that of water (0.800 g / cm³ ) and is slightly soluble therein, in proportion of 3 g / L . Its solubility is higher in alcohols and ethers , [ 5 ] being the value of the logarithm of its partition coefficient log P= 1.54, which reveals that it is more soluble in nonpolar solvents - such as n-octanol - than in water. [ 2 ] [ 6 ]
Synthesis and uses
4-methylpentanenitrile can be synthesized from 4-methylpent-2-enonitrile —with a yield of around 99% -, [ 7 ] making use of a reducing system comprising phenylsilane and a Mo (CO 6 ) catalyst in tetrahydrofuran . [ 8 ] Another synthesis route consists of the hydro-2-propylation of acrylonitrile with 2-propylazodiphenylmethanol , a reaction that is enhanced by adding phenol . [ 9 ]In turn, 4-methylpentanenitrile is a precursor to other nitrogenous organic compounds such as 5-methyl-1-hexanamine or 2,4-dimethylpentanenitrile . [ 10 ]
4-methylpentanenitrile has been studied in relation to the synthesis of 1 H - pentasubstituted tetrazolium ; said synthesis can be carried out by a reaction between nitrile and sodium azide at 110 ° C in dimethyl sulfoxide using cuttlebone as catalyst , [ 11 ] or by reacting the nitrile with [bmim] N 3 in the presence of expanded perlite . [ 12 ]
On the other hand, the use of this nitrile as an electrode binder has been proposed , being useful in the assembly of lithium-ion battery electrodes . [ 13 ] It can also be used in the manufacture of sulfide glass and ceramic of this same material. [ 14 ]
The following compounds are isomers of 4-methylpentanenitrile:
- CAS number
- 4-Methylpentanenitrile (ChemSpider)
- Isocapronitrile (PubChem)
- Isocapronitrile (Chemical Book)
- Isocapronitrile. Safety Data Sheet (TCI Chemicals)
- Pentanenitrile, 4-methyl- (EPA)
- Synthesis Route for 542-54-1 (Molbase)
- Keinan, E; Perez, P. (1987). «Silicon hydrides and molybdenum(0) catalyst: a novel approach for conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds». J Org Chem. 52 (12): 2576-2580. Consultado el 22 de febrero de 2017.
- Roberts, J.T.; Rittberg, B.R.; Kovacic, P. (1980). «Synthetic applications of α-hydroxydiazenes. III. Uncatalyzed and phenol catalyzed hydroalkylation of alkenes and of azobenzene with alkylazodiphenylmethanols». Canadian Journal of Chemistry 58 (22): 2386-23935. Consultado el 24 de febrero de 2017.
- 4-methylpentanenitrile 542-54-1: Precursor and Downstream Products
- Ghodsinia, S.; Akhlaghinia, B. (2015). «A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high effective and low cost heterogeneous catalyst». RSC Advances 5 (62): 49849-49860. Consultado el 24 de febrero de 2017.
- Jahanshahi, R.; Akhlaghinia, B. (2015). «Expanded perlite: an inexpensive natural efficient heterogeneous catalyst for the green and highly accelerated solvent-free synthesis of 5-substituted-1H-tetrazoles using [bmim]N3 and nitriles». RSC Advances 5 (126): 104087-104094. Consultado el 24 de febrero de 2017.
- ELECTRODE BINDER COMPOSITION FOR LITHIUM ION ELECTRICAL STORAGE DEVICES (2015). Hellring, Stuart D.; et al. Patente US 20150280238
- SULFIDE GLASS, AND METHOD FOR PRODUCING SULFIDE GLASS CERAMIC (2015). Aburatani; Ryo; Junke; Tadanori. Patente US 2015/0207170