Heptanonitrilo - Heptanonitrilo

Heptanonitrilo
Heptanonitrilo.tif
Heptanonitrilo-3D.gif
IUPAC name
heptanonitrilo
General
Other names 1-cyanohexano
heptylnitrile
hexylcyanuro
enantonitrile
3-phenylpropionitrilo
Semi-developed formula CH 3 - (CH 2 ) 5 - C≡N
Molecular formula C 7 H 13 N
Identifiers
CAS number 629-08-3[1]
RTECS number MW5604750
ChEMBL CHEMBL1231869
ChemSpider 11866
PubChem 12372
SOME UA4Z3QT98A
Physical properties
Appearance Clear yellow liquid
Density 810 kg/; 0,81 g/cm³
Molar mass 111.19 g / mol
Melting point −64 °C (209 K)
Boiling point 186 °C (459 K)
Vapor pressure 0,7 ± 0,4 mmHg
Refractive index (n D ) 1,419
Chemical properties
Solubility in water 400 mg / L
log P 2,21
Family Nitrilo
Dangerousness
Flash point 331,15 K (58 °C)
NFPA 704

NFPA 704.svg

2
3
0
Related compounds
nitrilos hexanonitrile
octanonitrile
nonanonitrile
dinitrilos heptanodinitrilo
trinitrilos 1,3,5-pentanotricarbonitrilo
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The heptanenitrile , also called 1-cyanohexane , enantonitrilo or 3-phenylpropionitrile , [ 2 ] [ 3 ] is a nitrile whose molecular formula is C 7 H 13 N .

Physical and chemical properties

At room temperature , Heptanonitrile is a clear yellow liquid . [ 4 ] It has its boiling point at 186 ° C and its melting point at -64 ° C. It has a density lower than water (ρ = 0.810 g / cm³ ) and is slightly soluble therein, in proportion of 400 mg / L . [ 5 ] In this sense, the value of the logarithm of its partition coefficient , log P= 2.21, indicates that it is considerably more soluble in nonpolar solvents - such as octanol - than in water. It has a surface tension of 29.0 ± 5.0 dyne / cm , similar to that of other linear alkyl nitriles. [ 2 ] [ 6 ]

Heptanonitrile is incompatible with oxidizing and reducing agents , as well as with strong acids and bases . [ 7 ]

Synthesis

Heptanonitrile is synthesized by adding 1-chlorohexane to a mixture of sodium cyanide in dimethyl sulfoxide previously heated to 90 ° C; to the reaction being exothermic , the temperature should be kept below 160 ° C: [ 8 ]

Preparation of heptanenitrile.tif

Another way to obtain heptanonitrile is by pyrolysis of N, N- dichloroheptanamine carried out during gas-liquid chromatography at 190-280 ° C. [ 9 ] A different synthetic route used as the precursor 2-bromoheptanenitrile , with a yield around 99% -, [ 10 ] using a catalyst of copper (I) .

Also, the combination of o-iodoxibenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) efficiently oxidizes 1-heptanamine to heptanonitrile under mild conditions. Other oxidizing agents used to transform amines to nitriles are lead tetraacetate , silver oxide , cobalt and nickel peroxide , or osmium tetroxide ; Metal-free reagents such as sodium hypochlorite or molecular iodine can also be used . [ 11 ] Conversely, reduction of heptanonitrile at 25 ° C with In Cl 3 /NaBH 4 in tetrahydrofuran , allows to obtain 1-heptanamine with a yield of 87%. [ 12 ]

Applications

Heptanonitrile has been investigated in relation to inclusion complexes in order to evaluate the contribution of hydrophilic parts of host molecules in aliphatic inclusion complexes; In this sense, the thermodynamic properties of the inclusion complexes of cyclodextrin (α-CD) with aliphatic nitriles - among them heptanonitrile - were determined in aqueous solutions. [ 13 ]

Regarding its uses, heptanonitrile is used in the synthesis of 2,3,5,6-tetrahexylpyrazine [ 7 ] and also appears as an intermediate in the manufacture of pharmaceutical products. [ 4 ] Thus, it appears as a precursor in the synthesis of certain quinoline lactams that bind to benzodiazepine receptors, used as anxiolytic agents . [ 14 ]

The use of this nitrile as a solvent in chemical vapor deposition (CVD) has also been proposed when making thin sheets of ruthenium components used as electrodes in computer memory devices ( DRAM ) or in diamagnetic films of hard drives . [ 15 ] It can also serve as a solvent in organic electroluminescence systems . [ 16 ] It can also be used for the production of semiconductor deviceswhich include a nickel foil . [ 17 ]

Precautions

This compound is a flammable product —both in liquid and vapor form—, with a flash point of 58 ° C. Burning releases toxic gases such as nitrogen oxides , carbon monoxide, and hydrogen cyanide . Contact with skin and eyes should be avoided as it causes skin irritation and severe eye irritation. [ 18 ] [ 3 ]

See also

References

  1. CAS number
  2. a b Heptanonitril (ChemSpider)
  3. a b Heptanenitrile (PubChem)
  4. a b 3-phenylpropionitrie (Chemical Book)
  5. Heptanenitrile (EPA)
  6. Heptanenitrile (ChemSynthesis)
  7. a b A12326 Heptanenitrile, 98% (Alfa Aesar)
  8. Preparation of heptanenitrile (PrepChem)
  9. Roberts, J.T.; Rittberg, B.R.; Kovacic, P. (1981). «Chemistry of N-halo compounds. 33. Pyrolytic eliminations from N,N-dichloro derivatives of primary, secondary, and tertiary alkyl primary amines». J. Org. Chem. 46 (21): 4111-4115. Consultado el 20 de febrero de 2017.
  10. Synthesis Route for 629-08-3 (Molbase)
  11. Drouet, Fleur; Fontaine, Patrice; Masson, Geraldine; Zhu, Jieping (2009). «IBX/TBAB-Mediated Oxidation of Primary Amines to Nitriles». Synthesis 8: 1370-1374. Consultado el 15 de marzo de 2017.
  12. Jaime Z. Saavedra, Angel Resendez, Alexander Rovira, Scott Eagon, Dustin Haddenham, Bakthan Singaram (2012). «Reaction of InCl3 with Various Reducing Agents: InCl3–NaBH4-Mediated Reduction of Aromatic and Aliphatic Nitriles to Primary Amines». J. Org. Chem. 77 (1): 221-228. Consultado el 15 de julio de 2016.
  13. Takayoshi Kimura, Takashi Yukiyama, Masao Fujisawa (2012). «Thermodynamic properties of inclusion complexes of α-cyclodextrin + aliphatic nitriles (H(CH2)nCN: n = 1–8) in aqueous solution». Journal of Thermal Analysis and Calorimetry 108 (2): 695-704. Consultado el 31 de marzo de 2017.
  14. Tetrahydropyridoquinolone derivatives useful as anxiolytic agents. James B. Campbell (1992). Patente US 5118688 A.
  15. RUTHENIUM COMPOUND, MATERIAL FOR THIN FILM FORMATION, AND PROCESS FOR THIN FILM FORMATION (2016). Hatase; Masako; et al. Patente US 2016/0272664
  16. Method for producing electroluminescence device (2015). Kakimoto, H.; et al. Patente US 9,093,667
  17. Method of manufacturing semiconductor device including nickel-containing film (2016). Youn et al. Patente US 9,391,089
  18. ^ «1-Cyanohexane. Pfaltz and Bauer (Safety Sheet). » . Archived from the original on March 7, 2017 . Accessed March 6, 2017 .