4385-04-0

Basic information

• Product Name: N,N-DIMETHYLHEXYLAMINE
• Synonyms: N-(N-HEXYL)DIMETHYLAMINE;N,N-DIMETHYLHEXYLAMINE;1-(DIMETHYLAMINO)HEXANE;1-Hexanamine, N,N-dimethyl-;Hexanamine, N,N-dimethyl;N,N-Dimethyl-1-hexanamine;N,N-Dimethyl-n-hexylamine;N,N-Dimethylhexylamine,99%
• CAS NO: 4385-04-0
• Molecular Formula: C₈H₁₉N
• Molecular Weight: 129.24
• EINECS: 224-491-8
• Product Categories: Amines;C8;Nitrogen Compounds
• Mol File: 4385-04-0.mol

Chemical Properties

• Melting Point: -76.53°C (estimate)
• Boiling Point: 146-150 °C(lit.)
• Flash Point: 92 °F
• Appearance: Clear colorless/Liquid
• Density: 0.744 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.49mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with methanol.
• PKA: 9.99±0.28(Predicted)
• Stability: Stable. Flammable. Incompatible with strong acids, strong oxidizing agents.
• BRN: 1732757
• CAS DataBase Reference: N,N-DIMETHYLHEXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYLHEXYLAMINE(4385-04-0)
• EPA Substance Registry System: N,N-DIMETHYLHEXYLAMINE(4385-04-0)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2733 3/PG 3
• WGK Germany: 3
• F: 9
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4385-04-0(Hazardous Substances Data)

Usage

Uses

1. Analytical Chemistry:
N,N-Dimethylhexylamine is used as an ion-pairing agent for studying the poor retention of uridine diphosphate-linked intermediates on reverse phase media. This application aids in improving the analysis and understanding of these intermediates, which are crucial in various biochemical processes.
2. Food Industry:
In the food industry, specifically for baby foods, N,N-Dimethylhexylamine is utilized in determining the presence and concentration of five monophosphate nucleotides (cytidine 5′-monophosphate, uridine 5′-monophosphate, adenosine 5′-monophosphate, inosine 5′-monophosphate, and guanosine 5′-monophosphate). These nucleotides are essential for the proper development and functioning of the immune system in infants.
3. Pharmaceutical Industry:
Used in Cancer Treatment:
N,N-Dimethylhexylamine acts as an additive and is encapsulated into nanoparticles along with salinomycin (Sali), a compound with selective toxicity to cancer stem cells (CSCs). This combination enhances the delivery and effectiveness of salinomycin, targeting and eliminating CSCs, which are responsible for tumor recurrence and resistance to conventional cancer treatments.

Synthesis Reference(s)

Synthesis, p. 996, 1981 DOI: 10.1055/s-1981-29677

InChI:InChI=1/C8H19N/c1-4-5-6-7-8-9(2)3/h4-8H2,1-3H3/p+1

Upstream product

• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 7334-95-4 n-hexylammonium bromide 
• 120087-76-5 hexyl-trimethyl-ammonium; hydroxide 
• 111-26-2 hexan-1-amine 
• 111-25-1 1-bromo-hexane 
• 124-40-3 dimethyl amine 
• 67-56-1 methanol 
• 35161-70-7 N-methylhexanamine 
• 5830-30-8 N,N-dimethylhexanamide 
• 579-75-9 2-Methoxybenzoic acid 
• 2650-53-5 n-hexyltrimethylammonium bromide 
• 109-67-1 1-penten 
• 201230-82-2 carbon monoxide 

Downstream Products

• 29811-98-1 [2-(4-chloro-phenoxy)-ethyl]-hexyl-dimethyl-ammonium; bromide 
• 132753-65-2 [2-(2-chloro-phenoxy)-ethyl]-hexyl-dimethyl-ammonium; bromide 
• 107-43-7 betaine 
• 131409-91-1 hexyl-dimethyl-(2-phenoxy-ethyl)-ammonium; bromide 
• 34418-88-7 N,N-Dimethyl-n-hexylamin-N-oxid 
• 22559-57-5 hexyldimethylbenzylammonium chloride 
• 37615-53-5 N,N-dihexyl-N-methylamine 
• 111-27-3 hexan-1-ol 
• 143-16-8 dihexylamine 
• 102-86-3 tri-n-hexylamine 
• 1234679-35-6 Br^(1-)*C₂₈H₃₉N₂O₃⁽¹⁺⁾ 
• 1234679-42-5 Br^(1-)*C₃₂H₄₇N₂O₃⁽¹⁺⁾ 
• 66-25-1 hexanal 
• 124-40-3 dimethyl amine 

Relevant articles and documents

Green and chemo selective amine methylation using methanol by an organometallic ruthenium complex

Herein a green and convenient catalytic N-methylation of aniline and n-hexylamine using methanol as a dual methylation agent and solvent has been investigated. A new ruthenium carbonyl complex was synthesized and applied as a homogeneous catalyst in methylation reaction. The solid-state structure of the complex was determined by X-ray crystallographic analysis which indicate xantphos ligand bonded to ruthenium (II) as a tridentate pincer ligand by two P donor and one O atom. The catalytic system showed excellent conversion and selectivity toward N-methylaniline, and N,N-hexyldimethylamine at 140°C.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Efficient hydrogenation of aliphatic amides to amines over vanadium-modified rhodium supported catalyst

This work presents a highly efficient catalytic hydrogenation system developed for the selective transformation of tertiary N,N-dimethyldodecanamide and secondary azepan-2-one amides to the corresponding amines. Industrial hydrogenation catalysts Pd/Al2O3, Pt/Al2O3 and Rh/Al2O3 were modified with vanadium (V) or molybdenum (Mo) species as oxophilic centres. The modified catalysts were prepared by deposition of V or Mo precursor on supported catalysts via impregnation method. The catalysts were characterized by ICP-OES, XRD, XPS, H2-TPR, FTIR, CO-chemisorption, TEM, SEM-EDX and TGA. Modified Rh-V/Al2O3 catalyst displayed the best performance affording high yield and selectivity >95 % to the desired tertiary and secondary amines at moderate reaction conditions of T H2 0 sites and oxophilic Vδ+ sites in the bimetallic Rh-V/Al2O3 catalyst were determined to be beneficial for the selective dissociation of C[dbnd]O bond of the carboxamides into the desired amines.

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for N, N-Dimethylamine Derivatives

A new catalytic system for N,N-dimethylamination of primary alcohols using aqueous dimethylamine in the absence of additional organic solvents has been developed. The reaction proceeds via borrowing hydrogen processes, which are atom-efficient and environmentally benign. An iridium catalyst bearing an N-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable N,N-dimethylamine derivatives, including biologically active and pharmaceutical molecules, were synthesized. The practical application of this methodology was demonstrated by a gram-scale reaction.

Method for preparing tertiary amine organic compound by decomposing substituted formamide under mild condition

The invention discloses a method for preparing tertiary amine organic compounds by decomposing substituted formamide under mild conditions, which comprises the following steps: heating and stirring aldehydes serving as a reaction substrate, substituted formamide serving as a solvent, a reducing agent and an amination reagent, Ti-based oxide/hydroxide serving as a catalyst and a small amount of water serving as an auxiliary agent to generate the corresponding tertiary amine compound. Hydrogen is not needed in the reaction process. The method can be suitable for various aldehydes including aromatic aldehydes, fatty aldehydes and the like, and has the characteristics of high conversion rate and single product, and the tertiary amine compound can be simply, efficiently and safely synthesized without using hydrogen and noble metals in the reaction, so that the method has remarkable economic effects and application prospects.

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Scalable synthesis of salt-free quaternary ammonium carboxylate catanionic surfactants

Surfactants in commercial products commonly contain catanionic mixtures thus many studies of aqueous surfactant mixtures have been carried out. However, hardly any studies have been dedicated to pure catanionic surfactants often termed salt-free catanionic surfactants. One of the difficulties is in acquirement of samples with required purity due to difficult separation of these compounds from inorganic salts. In this work we present an alternative method of synthesis using dimethyl carbonate as the alkylating agent in order to obtain alkyl trimethylammonium alkanecarboxylates with medium alkyl chain lengths (6-10).

Photon-initiated heterogeneous redox couples for methylation of anilines under mild conditions

Methylation of anilines has drawn a lot of attention due to their valuable applications and directly using methanol as a methylation reagent is of great advantage. Photon-initiated heterogeneous catalysis of this methylation process meets the requirements of green chemistry. Herein we show that balanced redox zones within carbon nitride supported Pd nanoparticles boost the selectivity of methylation of anilines under mild conditions.

The selective reductive amination of aliphatic aldehydes and cycloaliphatic ketones with tetragonal zirconium dioxide as the heterogeneous catalyst

A selective reductive amination of aliphatic aldehydes and cycloaliphatic ketones is achieved with tetragonal zirconium dioxide (t-ZrO2) as the catalyst. With N, N-dimethyl formamide (DMF) as the solvent, low-molecular-weight amine source and reductant, a more than 99 percent yield of N, N-dimethylpentan-1-amine or N, N-dimethyl cyclohexanamine was obtained when n-pentanal or cyclohexanone was used as the substrate. Particularly, the crystallographic structures exhibit a significant effect on catalytic performance where the tetragonal crystalline was preferable to monoclinic one during the reductive amination reaction. In addition, the recycling experiments of catalysts indicate that t-ZrO2 still kept a high catalytic activity even after being reused five times. From the result of DFT calculations, it is concluded that the crystalline of zirconium dioxide is closely related to the charge transferring rate between the catalyst and the adsorbed reactant. Finally, based on the experiment phenomena and simulation result, a possible reaction mechanism is proposed for the reductive amination of cyclohexanone.