17373-27-2

Basic information

• Product Name: N,N-DIMETHYLNONYLAMINE
• Synonyms: 1-(DIMETHYLAMINO)NONANE;N N-DIMETHYL-N-NONYLAMINE;N,N-DIMETHYLNONYLAMINE;.,N-DIMETHYLNONYLAMINE, 97%
• CAS NO: 17373-27-2
• Molecular Formula: C₁₁H₂₅N
• Molecular Weight: 171.32
• Mol File: 17373-27-2.mol

Chemical Properties

• Melting Point: -72.57°C (rough estimate)
• Boiling Point: 83 °C7 mm Hg(lit.)
• Flash Point: 76 °C
• Appearance: /
• Density: 0.773 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.179mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• BRN: 1736553
• CAS DataBase Reference: N,N-DIMETHYLNONYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYLNONYLAMINE(17373-27-2)
• EPA Substance Registry System: N,N-DIMETHYLNONYLAMINE(17373-27-2)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 23-24/25
• RIDADR: UN 1993 / PGIII
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 17373-27-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dimethylnonylamine is used as a charge modifier for the separation of enantiomers of anti-inflammatory drugs. It plays a crucial role in chiral chromatography, where it helps in the resolution of enantiomers, which are essential for ensuring the desired therapeutic effects and minimizing potential side effects of chiral drugs.
Used in Chemical Synthesis:
N,N-Dimethylnonylamine is also used for the synthesis of bromoethylnonyldimethylammonium bromide, which is a quaternary ammonium compound with potential applications in various fields, such as antimicrobial agents, phase-transfer catalysts, and surfactants. The synthesis of N,N-DIMETHYLNONYLAMINE involves the reaction of N,N-dimethylnonylamine with bromoethyl bromide, resulting in the formation of the desired quaternary ammonium compound.

InChI:InChI=1/C11H25N/c1-4-5-6-7-8-9-10-11-12(2)3/h4-11H2,1-3H3

Upstream product

• 6225-08-7 octanecarboxylic acid dimethylamide 
• 7732-18-5 water 
• 108758-41-4 1,1-dimethyl-decahydro-azecinium; iodide 
• 112-20-9 n-Nonylamin 
• 124-38-9 carbon dioxide 
• 111-66-0 oct-1-ene 
• 107-31-3 Methyl formate 
• 124-40-3 dimethyl amine 
• 64-18-6 formic acid 
• 143-08-8 nonyl alcohol 
• 201230-82-2 carbon monoxide 
• 629-27-6 1-Iodooctane 
• 764-85-2 Nonanoyl chloride 
• 693-58-3 1-Bromononane 

Downstream Products

• 3024-71-3 N-benzyl-N,N-dimethylnonan-1-aminium chloride 
• 1234679-37-8 Br^(1-)*C₃₁H₄₅N₂O₃⁽¹⁺⁾ 
• 1234679-45-8 Br^(1-)*C₃₅H₅₃N₂O₃⁽¹⁺⁾ 
• 19041-07-7 (CH₃)2N(C₉H₁₉)BH₃ 
• 121-44-8 triethylamine 
• 92764-21-1 3-(nonyldimethylammonio)propyl sulfate 
• 37074-52-5 N,N,N-trimethylnonylammonium iodide 

Relevant articles and documents

Synthesis, SAR and pharmacological characterization of novel anthraquinone cation compounds as potential anticancer agents

Emodin, a natural anthraquinone derivative isolated from Rheum palmatum L., has been demonstrated to exhibit good anti-cancer effect. In this study, a series of novel quaternary ammonium salts of emodin, anthraquinone and anthrone were synthesized and their anticancer activities were tested in vitro. The effects of emodin quaternary ammonium salts on cell viability, apoptosis, intracellular ROS, and mitochondrial membrane potential were investigated in A375, BGC-823, HepG2 and HELF cells. The results demonstrated that compound 4a induced morphological changes and decreased cell viability. Apoptosis triggered by compound 4a was visualized using DAPI staining and Annexin V-FITC/PI staining. Compound 4a-induced apoptosis of A375 cells were showed to be associated with the dissipation of mitochondrial membrane potential (ΔΨm) as a result of the up-regulation of P53 and Caspase-3. When cancer cells were treated with emodin derivative, their ability to generate reactive oxygen species (ROS) rose significantly and the mitochondrial membrane potential decreased. Additionally, confocal microscopy assay confirmed that compound 4a was primarily located in the mitochondria of A375 cells. These results suggested that compound 4a has the potential for use in cancer therapy.

Fast continuous alcohol amination employing a hydrogen borrowing protocol

A continuous flow method for the direct conversion of alcohols to amines via a hydrogen borrowing approach is reported. The method utilises a low loading (0.5%) of a commercial catalyst system ([Ru(p-cymene)Cl2]2 and DPEPhos), reagent grade solvent and is selective for primary alcohols. Successful methylation of amines using methanol and the direct dimethylamination of alcohols using commercial dimethylamine solution are reported. The synthesis of two pharmaceutical agents Piribedil (5) and Buspirone (25) were accomplished in good yields employing these new methods.

General catalytic methylation of amines with formic acid under mild reaction conditions

A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines including [N-13C]-labelled drugs in good to excellent yields under mild conditions. Methylation made easy: A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines, including [N-13C]-labelled drugs, in good to excellent yields at mild conditions (see scheme; dppp=(1,3-bis(diphenylphosphino)propane)).

Methylformate as replacement of syngas in one-pot catalytic synthesis of amines from olefins

A new general approach for the one-pot hydroaminomethylation of olefins using methylformate as formylating agent instead of synthesis gas (syngas) has been proposed. Herein we report that a Ru-Rh catalytic system demonstrates high activity in a tandem conversion of a series of n-alkenes into amines using methylformate with yields 58-92% (6 h). The selectivity for the normal amine reached 96% with catalysis by the Ru carbonyl complex Ru3(CO) 12, with an overall yield of 55% with respect to amine in this instance. The addition of the Rh complex to Ru catalytic system, sharply increased the hydroaminomethylation rate of both the terminal and internal alkenes and increased the yield of amines to 82-93% (6-12 h). The Royal Society of Chemistry.

Selective methylation of amines with carbon dioxide and H2

Put a label on it: Carbon dioxide with H2 is shown to be an efficient and selective methylation reagent for aromatic and aliphatic amines (see scheme; acac=acetylacetonate, triphos = 1,1,1- tris(diphenylphosphanylmethyl)ethane). A variety of functionalized amines including 13C-labelled drugs were obtained with good yields and functional-group tolerance. Copyright

Efficient and regioselective ruthenium-catalyzed hydro-aminomethylation of olefins

An efficient and regioselective ruthenium-catalyzed hydroaminomethlyation of olefins is reported. Key to success is the use of specific 2-phosphino-substituted imidazole ligands and triruthenium dodecacarbonyl as catalyst. Both industrially important alip

Concentration of hydrophobic organic compounds and extraction of protein using alkylammoniosulfate zwitterionic surfactant mediated phase separations (cloud point extractions)

The zwitterionic surfactants 3-[nonyl- (or decyl-) dimethylammonio]propyl sulfate, (C9-APSO4 or C10-APSO4) were synthesized using Nilsson's procedure, and their phase separation behavior under different experimental conditions was evaluated. The results indicate that such zwitterionic surfactants can be utilized for the extraction/preconcentration of hydrophobic species in a manner akin to that previously reported for nonionic surfactants. This was demonstrated for several practical applications including the extraction/preconcentration of some steroidal hormones and vitamin E prior to high-performance liquid chromatography analysis. The zwitterionic surfactant mediated phase separation was also applied to the extraction of the hydrophobic membrane protein, bacterio-rhodopsin, from the hydrophilic cytochrome c protein, both originally present In an aqueous phase. The concentration factors for this aqueous two-phase extraction technique using C10-APSO4 ranged from 26 to 35 with recoveries In the range 88 to > 96%. Some comparative studies Indicate that the use of zwittterionic surfactants In lieu of nonionic surfactants (e.g. polyoxyethylene(7.5) nonyl phenyl ether PONPE-7.5) In such an extraction method offers some significant advantages such as purer, homogeneous surfactant preparation, minimum background absorbance at UV detection wavelengths, the two-phase region occurring at lower temperatures, and greater extraction efficiencies/concentration factors among others.