4528-39-6

Basic information

• Product Name: 2-ETHYL CAPRONITRILE
• Synonyms: 2-ETHYL CAPRONITRILE;2-Ethylhexanonitrile;NSC44904
• CAS NO: 4528-39-6
• Molecular Formula: C₈H₁₅N
• Molecular Weight: 125.21
• Mol File: 4528-39-6.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 193°Cat760mmHg
• Flash Point: 82.3°C
• Appearance: /
• Density: 0.811g/cm³
• Vapor Pressure: 0.475mmHg at 25°C
• Refractive Index: 1.419
• CAS DataBase Reference: 2-ETHYL CAPRONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHYL CAPRONITRILE(4528-39-6)
• EPA Substance Registry System: 2-ETHYL CAPRONITRILE(4528-39-6)

Safety Data

• Hazardous Substances Data: 4528-39-6(Hazardous Substances Data)

Usage

Preparation

In a 1-L round-bottomed flask, fitted with an efficient reflux condenser, were placed 2-ethylhexaneamide 1455 (286 g, 2 mol), dry benzene (300 mL), and thionyl chloride (357 g, 218 mL, 3 mol). The flask was placed in a water bath, which was quickly heated to 75–80 C° and maintained at that temperature for 4.5 h. The reaction mixture was then transferred to a 1.5-L beaker and cooled in an ice bath. A mixture of crushed ice (100 g) and water (100 mL) was added to decompose the excess thionyl chloride. Cold 50% aq. potassium hydroxide solution was then added in small portions with stirring until the mixture was alkaline to litmus. The basified mixture was then transferred to a separatory funnel, and the layers were separated. The aqueous portion was extracted with benzene (100 mL). The benzene solutions were combined and washed with 1% sodium carbonate solution (150 mL) and water (2 × 150 mL). The mixture was distilled from a modified Claisen flask, the bulk of the solvent being removed at atmospheric pressure. The yield of nitrile 1456 was 215–236 g (86–94%); bp 118–120 C°/100 mmHg.

InChI:InChI=1/C8H15N/c1-3-5-6-8(4-2)7-9/h8H,3-6H2,1-2H3

Upstream product

• 4164-92-5 (-)(R)-heptane-carboxylic acid-(3)-amide 
• 109-74-0 propyl cyanide 
• 109-69-3 n-Butyl chloride 
• 104-76-7 2-Ethylhexyl alcohol 
• 4164-92-5 2-ethyl-hexanamide 
• 109-65-9 1-bromo-butane 
• 542-69-8 1-iodo-butane 
• 628-73-9 hexanenitrile 
• 74-85-1 ethene 
• 34612-83-4 2-ethyl-hexanal oxime 
• 59346-59-7 2-ethyl-hexanal-dimethylhydrazone 
• 58955-90-1 iso‐octyl azide 
• 104-75-6 2-Ethylhexylamine 
• 123-05-7 d,l-2-ethylhexanal 

Downstream Products

• 7512-65-4 2-ethyl-2-chloro-hexanoic acid amide 
• 16493-80-4 4-ethyloctanoic acid 

Relevant articles and documents

Synthesis, characterization, catalytic and biological application of half-sandwich ruthenium complexes bearing hemilabile (κ2-: C, S)-thioether-functionalised NHC ligands

A series of cationic Ru(ii)(η6-p-cymene) complexes with thioether-functionalised N-heterocyclic carbene ligands have been prepared and fully characterized. Steric and electronic influence of the R thioether substituent on the coordination of the sulfur atom was investigated. The molecular structure of three of them has been determined by means of X-ray diffractrometry and confirmed the bidentate (κ2-C,S) coordination mode of the ligand. Interestingly, only a single diastereomer, as an enantiomeric couple, was observed in the solid state for complexes 1c, 1i and 1j. DFT calculations established a low energy inversion barrier between the two diastereomers through a sulfur pyramidal inversion pathway with R donating group while a dissociative/associative mechanism is more likely with R substituents that contain electron withdrawing group, thus suggesting that the only species observed by the 1H-NMR correspond to an average resonance position of a fluxional mixtures of isomers. All these complexes were found to catalyse the oxydant-free double dehydrogenation of primary amine into nitrile. Ru complex bearing NHC-functionalised S-tBu group was further investigated in a wide range of amines and was found more selective for alkyl amine substrates than for benzylamine derivatives. Finally, preliminary results of the biological effects on various human cancer cells of four selected Ru complexes are reported.

Direct Synthesis of Nitriles from Carboxylic Acids Using Indium-Catalyzed Transnitrilation: Mechanistic and Kinetic Study

Aliphatic and aromatic carboxylic acids can be quantitatively converted to the corresponding nitriles in the presence of catalysts using acetonitrile both as a solvent and reactant at 200 °C. This transformation is based on the acid-nitrile exchange (i.e., transnitrilation) and uses a nontoxic and water resistant catalyst, indium trichloride (InCl3). The mechanism of the transnitrilation was investigated both experimentally and computationally and compared to the previously proposed mechanism. In contrast to the usually assumed formation of amide as an intermediate, transnitrilation is an equilibrium reaction and proceeds via an equilibrated Mumm reaction with the formation of an imide as an intermediate. A simple and reversible mechanism was proposed for this reaction, which was validated by kinetics measurement and by density functional theory calculations of the reaction intermediates and reaction mechanisms.

Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.