5585-39-7

Usage

Uses

Used in Food Industry:
(E)-3,7-Dimethyl-2,6-octadienenitrile is used as a flavoring agent for its fruity and floral aroma, enhancing the taste and smell of various food products.
Used in Perfume and Fragrance Industry:
(E)-3,7-Dimethyl-2,6-octadienenitrile is utilized in the production of perfumes and fragrances, contributing to the creation of complex and appealing scents for personal and household products.
Used in Pharmaceutical Industry:
(E)-3,7-Dimethyl-2,6-octadienenitrile is employed in the synthesis of pharmaceuticals, serving as a key intermediate in the development of various medicinal compounds.
Used in Chemical Synthesis:
It is also used in the synthesis of other organic compounds, highlighting its versatility as a building block in organic chemistry.
Used in Rubber and Plastics Industry:
(E)-3,7-Dimethyl-2,6-octadienenitrile finds application in the manufacturing of rubber and plastic products, where it may contribute to the modification of material properties.

InChI:InChI=1/C10H15N/c1-9(2)5-4-6-10(3)7-8-11/h5,7H,4,6H2,1-3H3

Upstream product

• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 106-24-1 Geraniol 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 6246-48-6 geranylamine 
• 870-63-3 prenyl bromide 
• 624-15-7 geraniol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 372-09-8 cyanoacetic acid 
• 35278-77-4 geranylamine 
• 23089-87-4 5-methyl-4-hexenenitrile 

Downstream Products

• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 6890-91-1 (3RS,all-E)-hydroxyretinal 
• 42926-75-0 2,6,6-trimethyl-4-hydroxy-1-cyclohexene-1-carboxaldehyde 
• 72152-84-2 2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile 
• 145106-79-2 3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbonitrile 
• 264279-20-1 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile 
• 57524-13-7 2,6,6-trimethyl-2-cyclohexenecarbonitrile 
• 40188-41-8 3,7-dimethyloctanenitrile 
• 51566-62-2 citronellylnitrile 
• 5258-61-7 tris-(3,7-dimethyl-octyl)-amine 
• 79-77-6 (E)-β-ionone 
• 141-10-6 pseudoionone 

Relevant academic research and scientific papers

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine

Herein, we demonstrate the on-demand synthesis of chloramine from aqueous ammonia and sodium hypochlorite solutions, and its subsequent utilization as an ambiphilic nitrogen source in continuous-flow synthesis. Despite its advantages in cost and atom economy, chloramine has not seen widespread use in batch synthesis due to its unstable and hazardous nature. Continuous-flow chemistry, however, provides an excellent platform for generating and handling chloramine in a safe, reliable, and inexpensive manner. Unsaturated aldehydes are converted to valuable aziridines and nitriles, and thioethers are converted to sulfoxides, in moderate to good yields and exceedingly short reaction times. In this telescoped process, chloramine is generated in situ and immediately used, providing safe and efficient conditions for reaction scale-up while mitigating the issue of its decomposition over time.

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.

Easy Ruthenium-Catalysed Oxidation of Primary Amines to Nitriles under Oxidant-Free Conditions

A dehydrogenation of primary amine to give the corresponding nitrile under oxidant- and base-free conditions catalysed by simple [Ru(p-cym)Cl2]2 with no extra ligand is reported. The system is highly selective for alkyl amines, whereas benzylamine derivatives gave the nitrile product together with the imine in a ratio ranging from 14:1 to 4:1 depending on the substrate. Preliminary mechanistic investigations have been performed to identify the key factors that govern the selectivity.

Method for Selective Oxidation of Amines Using Two Dimensional Heterogeneous Nano-catalysts with Ruthenium Dispersed on Exfoliated Sheets of Molybdenum Disulfide

Disclosed is a method for selectively oxidizing an amine-based compound to convert the same into compounds such as nitrile using a two-dimensional heterogeneous nanocatalyst containing ruthenium supported, at high dispersion rate, on an exfoliated layer of molybdenum disulfide which is a layered transition metal dichalcogenide (LTMD).COPYRIGHT KIPO 2019

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.

Selective aerobic oxidation of benzylic amines to aryl nitriles catalyzed by CuBr2/N-methyl imidazole

A convenient and efficient copper-catalyzed aerobic oxidation of primary amines to aryl nitriles was described. Various benzylic and allylic amines were selectively oxidized to the corresponding nitriles in high yields using CuBr2/NMI as the catalyst and O2 as the oxidant. The oxidation reaction profiles monitored by 1H NMR disclosed the scenario of the reaction path as well as the role of the additives. The addition of NMI increased the rate of reaction and suppressed the hydrolysis and the deamination.

Ligand controlled switchable selectivity in ruthenium catalyzed aerobic oxidation of primary amines

A ligand controlled catalytic system for the aerobic oxidation of 1° amines to nitriles and imines has been developed where the varying π-acidic feature of BIAN versus phen in the frameworks of ruthenium catalysts facilitates switchable selectivity.

Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration

All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two experimentally validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chemical boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation.

PROCESS FOR THE MANUFACTURE OF HYDROGENATED NITRILES

The present invention relates to the manufacture and the use of specific organic compounds of formula (II) wherein n is either 1 or 2, and wherein R1 is linear C1-4 alkyl or branched C3-4 alkyl, wherein R2 is hydrogen or linear C1-4 alkyl or branched C3-4 alkyl, as aroma ingredients in flavors and fragrances. Furthermore the invention relates to new specific organic compounds and their synthesis, as well as to flavor and fragrance formulations comprising at least one of the specific organic compounds.