Heptanonitrilo - Heptanonitrilo
|Semi-developed formula||CH 3 - (CH 2 ) 5 - C≡N|
|Molecular formula||C 7 H 13 N|
|Appearance||Clear yellow liquid|
|Density||810 kg/m³; 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|
|Solubility in water||400 mg / L|
|Flash point||331,15 K (58 °C)|
|NFPA 704|| |
|nitrilos|| hexanonitrile |
|Values in the SI and under standard conditions|
(25 ℃ and 1 atm ), unless otherwise indicated.
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 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 ]
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 ]
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 ]
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 ]
- CAS number
- Heptanonitril (ChemSpider)
- Heptanenitrile (PubChem)
- 3-phenylpropionitrie (Chemical Book)
- Heptanenitrile (EPA)
- Heptanenitrile (ChemSynthesis)
- A12326 Heptanenitrile, 98% (Alfa Aesar)
- Preparation of heptanenitrile (PrepChem)
- 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.
- Synthesis Route for 629-08-3 (Molbase)
- 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.
- 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.
- 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.
- Tetrahydropyridoquinolone derivatives useful as anxiolytic agents. James B. Campbell (1992). Patente US 5118688 A.
- RUTHENIUM COMPOUND, MATERIAL FOR THIN FILM FORMATION, AND PROCESS FOR THIN FILM FORMATION (2016). Hatase; Masako; et al. Patente US 2016/0272664
- Method for producing electroluminescence device (2015). Kakimoto, H.; et al. Patente US 9,093,667
- Method of manufacturing semiconductor device including nickel-containing film (2016). Youn et al. Patente US 9,391,089
- «1-Cyanohexane. Pfaltz and Bauer (Safety Sheet). » . Archived from the original on March 7, 2017 . Accessed March 6, 2017 .