10385-09-8

Basic information

• Product Name: N,N-diethylnonanamide
• CAS NO: 10385-09-8
• Molecular Formula: C₁₃H₂₇NO
• Molecular Weight: 213.3596
• Mol File: 10385-09-8.mol

Chemical Properties

• Boiling Point: 272.4°C at 760 mmHg
• Flash Point: 101.6°C
• Density: 0.862g/cm³
• Vapor Pressure: 0.00611mmHg at 25°C
• Refractive Index: 1.446
• CAS DataBase Reference: N,N-diethylnonanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-diethylnonanamide(10385-09-8)
• EPA Substance Registry System: N,N-diethylnonanamide(10385-09-8)

Safety Data

• Hazardous Substances Data: 10385-09-8(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
N,N-diethylnonanamide is used as a fragrance ingredient and masking agent for its ability to provide a mild, long-lasting odor in various formulations.
Used in Personal Care and Cosmetic Products:
N,N-diethylnonanamide is used as a fixative in perfumes and fragrances, enhancing their longevity and stability.
Used in Industrial Applications:
N,N-diethylnonanamide is used as a surfactant in emulsion formulations and as a dispersing agent, contributing to the stability and performance of various products.

Upstream product

• 764-85-2 Nonanoyl chloride 
• 109-89-7 diethylamine 
• 629-27-6 1-Iodooctane 
• 201230-82-2 carbon monoxide 
• 592-76-7 1-Heptene 
• 2430-01-5 2-bromo-N,N-diethylacetamide 

Downstream Products

• 74-84-0 ethane 
• 2216-87-7 undecan-3-one 

Relevant articles and documents

Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin

Atom transfer carbonylation (ATC) of alkyl iodides leading to carboxylic acid esters is effectively accelerated by Pd(PPh3)4 and Mn2(CO)10 under photoirradiation conditions. In the presence of amines, Pd(0) complexes affected double carbonylations leading to α-keto amides, whereas Mn2(CO)10 accelerated only a single carbonylation reaction leading to the corresponding amides. The Pd(0)-accelerated ATC system was successfully applied to the synthesis of hinokinin and dihydrocapsaicin.

Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization

Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.

Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction

A synthetically convenient approach for the direct α-deuteration of amides is reported. This mechanistically unusual process relies on a retro-ene-type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional-group tolerance and high deuterium incorporation.

Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides

A suite of flexible and chemoselective methods for the transition-metal-free oxidation of amides to α-keto amides and α-hydroxy amides is presented. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance. The utility of the method is showcased by the formal synthesis of a potent histone deacetylase inhibitor.

Pd/light-accelerated atom-transfer carbonylation of alkyl iodides: Applications in multicomponent coupling processes leading to functionalized carboxylic acid derivatives

The atom-transfer carbonylation reaction of various alkyl iodides thereby leading to carboxylic acid esters was effectively accelerated by the addition of transition-metal catalysts under photoirradiation conditions. By using a combined Pd/hv reaction system, vicinal C-functionalization of alkenes was attained in which α-substituted iodoalkanes, alkenes, carbon monoxide, and alcohols were coupled to give functionalized esters. When alkenyl alcohols were used as acceptor alkenes, three-component coupling reactions, which were accompanied by intramolecular esterification, proceeded to give lactones. Pd-dimer complex [Pd2(CNMe)6][PF6]2, which is known to undergo homolysis under photoirradiation conditions, worked quite well as a catalyst in these three- or four-component coupling reactions. In this metal/radical hybrid system, both Pd radicals and acyl radicals are key players and a stereochemical study confirmed the carbonylation step proceeded through a radical carbonylation mechanism. Light, camera, ATCion: Atom-transfer carbonylation of alkyl iodides to afford carboxylic acid esters was accelerated by the addition of transition-metal catalysts under photoirradiation. The carbonylation step proceeded through a radical mechanism. Copyright

Atom transfer carbonylation using ionic liquids as reaction media

Photo-induced ATC reactions of RI, CO, and amines to produce amides, were examined using ionic liquids, such as [bmim]PF6 and [bmim]NTf2, as reaction media in the presence of a catalytic amount of a Pd-carbene complex. When the primary alkyl iodide was used, the yield of the amide was lowered due to competing SN2 reactions between RI and amines, whereas the reaction of the tertiary alkyl iodides was dependent on the structure of the substrates. ATC reactions of a wide variety of secondary RI proceeded smoothly when ionic liquids were used as reaction media. The Pd-catalyst and ionic liquid could also be recycled.