628-73-9

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 58, p. 2271, 1980 DOI: 10.1139/v80-365The Journal of Organic Chemistry, 46, p. 4111, 1981 DOI: 10.1021/jo00334a001

Purification Methods

Wash the nitrile twice with half-volumes of conc HCl, then with saturated aqueous NaHCO3, dry over MgSO4, filter and distil it. [Beilstein 2 H 324, 2 I 141, 2 II 286, 2 III 733, 2 IV 930.]

InChI:InChI=1/C6H11N/c1-2-3-4-5-6-7/h2-5H2,1H3

Upstream product

• 110-86-1 pyridine 
• 628-02-4 Caproamide 
• 98-09-9 benzenesulfonyl chloride 
• 187737-37-7 propene 
• 74-98-6 propane 
• 543-59-9 1-Chloropentane 
• 143-33-9 sodium cyanide 
• 123-66-0 Ethyl hexanoate 
• 64-17-5 ethanol 
• 110-53-2 1-Bromopentane 
• 151-50-8 potassium cyanide 
• 628-17-1 amyl iodide 
• 111-26-2 hexan-1-amine 
• 143-16-8 dihexylamine 

Downstream Products

• 110-43-0 n-pentyl methyl ketone 
• 43018-64-0 2-butyl-3-oxo-octanenitrile 
• 5665-89-4 1-(2,4,6-trihydroxyphenyl)hexan-1-one 
• 88924-67-8 2,4-dimethyl-6-hexanoyl-resorcinol 
• 101268-53-5 1-(2,4,6-trihydroxy-3-methyl-phenyl)-hexan-1-one 
• 57661-23-1 hexadecan-6-one 
• 942-92-7 caprophenone 
• 92779-83-4 1-phenyl-hexylamine 
• 111-31-9 Hexanethiol 
• 111-26-2 hexan-1-amine 
• 628-02-4 Caproamide 
• 108724-16-9 hexanamide oxime 
• 66-25-1 hexanal 
• 142-62-1 hexanoic acid 

Relevant academic research and scientific papers

Impact of sulfur heteroatoms on the activity of quaternary ammonium salts as phase transfer catalysts for nucleophilic displacement reactions

The application of a new class of alkylammonium salts as phase-transfer catalysts was investigated. These salts are tetra(4-thiaalkyl) ammonium bromides, and the key questions of the study focus on how the incorporation of a sulfur atom in the alkyl chains affects the efficacy of the salts as phase-transfer catalysts. Employing the nucleophilic substitution of cyanide for bromide on 1-bromopentane as a model reaction, reaction rate constants and activation energies are evaluated. The kinetic parameters obtained using the tetrathiaalkylammonium salts are compared to those obtained using their tetraalkylammonium analogs. The general trend is that the presence of sulfur in the alkyl chains reduces the reaction rates and increases activation energies. This trend is analyzed both in terms of computational modeling and experimental distribution coefficients to determine the cause of the slower reaction rates. Thiaquats are shown to distribute more into the aqueous phase than traditional quat salts of similar chain length, resulting in lower organic phase concentrations. Quantum calculations indicate stronger ion pairing for the thiaquats, increasing activation energies and slowing reaction rates. Thus, differences in rate enhancements are attributable both to phase distribution and ion pairing effects.

A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides

A simple approach for the preparation of symmetrical quaternary ammonium bromides employing thiol-ene click chemistry is used to synthesize tetra(4-thiaalkyl)ammonium bromides. This approach allows the incorporation of a variety of alkyl moieties onto the nitrogen center with a one-step synthesis involving easy work-up, no side reactions and environmentally friendly reagents. To elucidate information regarding the behaviour of this novel class of compounds, comparisons to tetraalkylammonium analogues have been made. These include melting points, activity as phase-transfer catalysts, and conformational predictions from computational modelling. All results are consistent in indicating stronger bonding between the quaternary cation and the anion for the salts with 4-thiaalkyl chains as compared to those with n-alkyl chains.

Chemoenzymatic one-pot reaction from carboxylic acid to nitrile: Via oxime

We report a new chemoenzymatic cascade starting with aldehyde synthesis by carboxylic acid reductase (CAR) followed by chemical in situ oxime formation. The final step to the nitrile is catalyzed by aldoxime dehydratase (Oxd). Full conversions of phenylacetic acid and hexanoic acid were achieved in a two-phase mode.

Method for dehydrating primary amide into nitriles under catalysis of cobalt

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.

METHOD FOR PRODUCING NITRILE

The present invention provides a method of producing a nitrile from a primary amide, characterized in that the primary amide is subjected to a dehydration reaction in a supercritical fluid in the presence of an acid catalyst. The present invention achieves the object of reducing the corrosion of a reactor and the thermal decomposition of raw materials, as well as provides the effect of improving the reaction rate and nitrile selectivity.

A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide

This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.

Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst

The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.

An Air-Stable N-Heterocyclic [PSiP] Pincer Iron Hydride and an Analogous Nitrogen Iron Hydride: Synthesis and Catalytic Dehydration of Primary Amides to Nitriles

An air-stable N-heterocyclic PSiP pincer iron hydride FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) (4) was synthesized by Si-H activation of a Ph-substituted [PSiP] pincer ligand. The analogous strong electron-donating iPr-substituted [PSiP] pincer ligand was prepared and introduced into iron complex to give an iron nitrogen complex FeH(N2)(PMe3)(SiPh(NCH2PiPr2)2C6H4) (6). Both 4 and 6 showed similar high efficiency for catalytic dehydration of primary amides to nitriles. Air-stable iron hydride 4 was the best catalyst for its stabilization and convenient preparation. A diverse range of cyano compounds including aromatic and aliphatic species was obtained in moderate to excellent yields. A plausible catalytic reaction mechanism was proposed.

Method for continuous preparation of nitriles by amides (by machine translation)

The method comprises the following steps: preparing a lead salt supported by a molecular sieve by a lead salt and a molecular sieve through an impregnation method; and filling a molecular sieve-loaded lead catalyst into a fixed bed reactor. The amide or amide solution is sent into a fixed bed reactor from the top of the fixed bed to be subjected to catalytic dehydration, and the obtained reaction product is led out from the bottom of the fixed bed. The reaction product is separated to obtain the crude product of the nitrile corresponding to the amide. A fixed bed continuous production process is adopted, the reaction process is simple, the production efficiency is high, the product post-treatment is simple, and industrial production is easy to realize. (by machine translation)

Method for continuous preparation of nitriles in a pipelined reactor (by machine translation)

The method comprises the following steps that a tin catalyst is coated on the inner wall of the pipeline reactor; and the method comprises the following steps: coating a tin catalyst on the inner wall of the pipeline reactor. The amide solution and the catalytic auxiliary agent are mixed and then sent to a pipeline reactor, and the amide is dehydrated to generate nitrile at the reaction pressure of 0.1 - 2.0 mpa and 100 - 200 °C reaction temperature. The resulting reaction product was separated to give the crude product of the nitrile to which the amide corresponded. In the pipeline reactor, the corresponding nitrile is continuously prepared under the action of the tin catalyst, a dehydrating agent is not needed, byproducts only are water, and three wastes are reduced. (by machine translation)