4-methylpentanonitrile - 4-metilpentanonitrilo

4-methylpentanonitrile
4-metilpentanonitrilo.tif
4-metilpentanonitrilo-3D.gif
IUPAC name
4-methylpentanonitrile
General
Other names isocapronitrile
4-methylvaleronitrile
isoamylcyanide
isopentylcyanide
Semi-developed formula CH 3 -CH 2 ( CH 3 ) - (CH 2 ) 3 - C≡N
Molecular formula C6H11N
Identifiers
CAS number 542-54-1[1]
RTECS number YV8588000
ChemSpider 11866
PubChem 10491
SOME J6BD44GTPJ
Physical properties
Appearance Liquid clear colorless
Density 800 kg/; 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
Chemical properties
Solubility in water 3 g/L
log P 1,54
Family Nitrilo
Dangerousness
Flash point 318,15 K (45 °C)
Related compounds
nitrilos valeronitrilo
pivalonitrilo
hexanonitrilo
5-hexenonitrilo
heptanonitrilo
dinitrilos adiponitrilo
3,3'-tiodipropionitrilo
trinitrilos tricianoaminopropeno
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 4-methylpentanenitrile , also known as isocapronitrilo and isoamilcianuro , [ 2 ] [ 3 ] [ 4 ] is a nitrile of molecular formula C 6 H 11 N .

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 ]

This nitrile is chemically incompatible with strong oxidizing agents . [ 5 ]

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 ]

Precautions

This compound is a flammable product , its flash point being 45ºC. It is toxic if inhaled or ingested, as well as causing irritation to the skin. [ 5 ]

See also

The following compounds are isomers of 4-methylpentanenitrile:

References

  1. CAS number
  2. a b 4-Methylpentanenitrile (ChemSpider)
  3. Isocapronitrile (PubChem)
  4. Isocapronitrile (Chemical Book)
  5. a b c Isocapronitrile. Safety Data Sheet (TCI Chemicals)
  6. Pentanenitrile, 4-methyl- (EPA)
  7. Synthesis Route for 542-54-1 (Molbase)
  8. 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.
  9. 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.
  10. 4-methylpentanenitrile 542-54-1: Precursor and Downstream Products
  11. 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.
  12. 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.
  13. ELECTRODE BINDER COMPOSITION FOR LITHIUM ION ELECTRICAL STORAGE DEVICES (2015). Hellring, Stuart D.; et al. Patente US 20150280238
  14. SULFIDE GLASS, AND METHOD FOR PRODUCING SULFIDE GLASS CERAMIC (2015). Aburatani; Ryo; Junke; Tadanori. Patente US 2015/0207170