86-56-6

Usage

Uses

Used in Chemical Analysis:
N,N-Dimethyl-1-naphthylamine is used as a reagent in the detection and determination of nitrites. It plays a crucial role in the nitrate reductase test, where it reacts with a nitrite-sulfanilic acid complex to form a red precipitate of Prontosil. This reaction aids in identifying the presence and quantifying the amount of nitrites in a given sample.
Used in Environmental Testing:
In environmental applications, N,N-Dimethyl-1-naphthylamine is utilized for the detection and measurement of nitrite levels in water and soil samples. This is important for monitoring water quality and understanding the nitrogen cycle in ecosystems, as well as assessing the impact of pollutants on the environment.
Used in Food Industry:
N,N-Dimethyl-1-naphthylamine is also employed in the food industry for the detection of nitrites, which are often used as preservatives in certain food products. By using N,N-Dimethyl-1-naphthylamine, food scientists and quality control professionals can ensure that nitrite levels are within safe and acceptable limits, thus maintaining product safety and quality.
Used in Pharmaceutical Research:
In the pharmaceutical sector, N,N-Dimethyl-1-naphthylamine may be used in research and development for the synthesis of various drugs and medicinal compounds. Its unique chemical properties make it a valuable intermediate in the creation of new pharmaceutical agents.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx

InChI:InChI=1/C12H13N/c1-13(2)12-9-5-7-10-6-3-4-8-11(10)12/h3-9H,1-2H3

Upstream product

• 67-56-1 methanol 
• 612-52-2 2-naphthylamine hydrochloride 
• 41791-46-2 [1]naphthylamine; hydrogen sulfate 
• 512-56-1 trimethyl phosphite 
• 134-32-7 1-amino-naphthalene 
• 74-83-9 methyl bromide 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 2350-79-0 N,N,N-trimethylnaphthalen-1-aminium iodide 
• 67530-30-7 N,N-dimethyl O-(2,4,6-trimethylphenyl-sulfonyl) hydroxylamine 
• 703-55-9 1-naphthylmagnesiumbromide 
• 50-00-0 formaldehyd 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 

Downstream Products

• 78062-03-0 4-Dimethylaminonaphthalene-1-carboxylic acid 
• 52912-75-1 dimethyl-[1]naphthyl-amine; compound with 1,3,5-trinitro-benzene 
• 68582-46-7 bis-(4-dimethylamino-[1]naphthyl)-phenyl-methane 
• 4643-33-8 N-methyl-N-(naphthalen-1-yl)benzamide 
• 108762-85-2 (4-dimethylamino-[1]naphthyl)-phenyl ketone 
• 195195-42-7 4-(4,4'-bis-dimethylamino-benzhydrylidene)-4H-naphthalen-1-one 
• 23097-31-6 2-(4-dimethylamino-naphthalen-1-ylazo)-3-methyl-4-phenyl-thiazolium; iodide 
• 23235-23-6 2-(4-dimethylamino-naphthalen-1-ylazo)-3-methyl-4-p-tolyl-thiazolium; iodide 
• 23097-36-1 4-(3-bromo-phenyl)-2-(4-dimethylamino-naphthalen-1-ylazo)-3-methyl-thiazolium; iodide 
• 23097-34-9 4-(4-chloro-phenyl)-2-(4-dimethylamino-naphthalen-1-ylazo)-3-methyl-thiazolium; iodide 
• 23097-35-0 4-(4-bromo-phenyl)-2-(4-dimethylamino-naphthalen-1-ylazo)-3-methyl-thiazolium; iodide 
• 23097-32-7 2-(4-dimethylamino-naphthalen-1-ylazo)-4-(4-methoxy-phenyl)-3-methyl-thiazolium; iodide 
• 23097-33-8 2-(4-dimethylamino-naphthalen-1-ylazo)-4-(4-ethoxy-phenyl)-3-methyl-thiazolium; iodide 
• 23097-37-2 2-(4-dimethylamino-naphthalen-1-ylazo)-3-methyl-4-(3-nitro-phenyl)-thiazolium; iodide 

Relevant academic research and scientific papers

Dirhodium-Catalyzed Chemo-and Site-Selective C-H Amidation of N, N-Dialkylanilines

A method for dirhodium-catalyzed C(sp 3)-H amidation of N, N-dimethylanilines was developed. Chemoselective C(sp 3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp 2)-H bonds of the electron-rich aromatic ring. Site-selective C(sp 3)-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-Alkylaniline derivatives with secondary, tertiary, and benzylic C(sp 3)-H bonds α to a nitrogen atom.

Preparation method of N-alkylated derivative of primary amine compound

The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.

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.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride

Photocatalytic water splitting technology (PWST) enables the direct use of water as appealing “liquid hydrogen source” for transfer hydrogenation reactions. Currently, the development of PWST-based transfer hydrogenations is still in an embryonic stage. Previous reports generally centered on the rational utilization of the in situ generated H-source (electrons) for hydrogenations, in which photogenerated holes were quenched by sacrificial reagents. Herein, the fully-utilization of the liquid H-source and holes during water splitting is presented for photo-reductive N-alkylation of nitro-aromatic compounds. In this integrate system, H-species in situ generated from water splitting were designed for nitroarenes reduction to produce amines, while alkanols were oxidized by holes for cascade alkylating of anilines as well as the generated secondary amines. More than 50 examples achieved with a broad range scope validate the universal applicability of this mild and sustainable coupling approach. The synthetic utility of this protocol was further demonstrated by the synthesis of existing pharmaceuticals via selective N-alkylation of amines. This strategy based on the sustainable water splitting technology highlights a significant and promising route for selective synthesis of valuable N-alkylated fine chemicals and pharmaceuticals from nitroarenes and amines with water and alkanols.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2for consecutiveN-methylation of amines

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2leading to consecutive doubleN-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles ofN-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards doubleN-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations.

Mn-Catalyzed Selective Double and Mono-N-Formylation and N-Methylation of Amines by using CO2

Functionalization of amines by using CO2 is of fundamental importance considering the abundance of amines and CO2. In this context, the catalytic formylation and methylation of amines represent convenient and successful protocols for selective CO2 utilization as a C1 building block. This study represents the first example of selective catalytic double N-formylation of aryl amines by using a dinuclear Mn complex in the presence of phenylsilane. This robust system also allows for selective formylation and methylation of amines under a range of conditions.

Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions

Herein, we reported a successful Suzuki-Miyaura coupling of dimethyl aryl amines to forge biaryl skeleton via Ni catalysis in the absence of directing groups and preactivation. This transformation proceeded with high efficiency in the presence of magnesium. Preliminary mechanism studies demonstrated dual roles of magnesium: (i) a reductant that reduced Ni(II) species to active Ni(I) catalyst; (ii) a unique promoter that facilitated the Ni(I)/Ni(III) catalytic cycle.