86-56-6

Basic information

• Product Name: N,N-Dimethyl-1-naphthylamine
• Synonyms: 1-Naphthyldimethylamine;α-Dimethylaminonaphthalene;N-DiMe thyl-1-naphthylaMine;N,N-DiMethyl-1-naphthylaMine, 99% 25ML;N,N-Dimethyl-1-naphthylamine;N,N-DIMETHYL-1-NAPHTHYLAMINE;N,N-DIMETHYL-ALPHA-NAPHTHYL AMINE;1-DIMETHYLAMINONAPHTHALENE
• CAS NO: 86-56-6
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• EINECS: 201-682-4
• Mol File: 86-56-6.mol
• Article Data: 36

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 139-140 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: brown/Liquid
• Density: 1.042 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00778mmHg at 25°C
• Refractive Index: n20/D 1.622(lit.)
• Storage Temp.: Store at RT.
• PKA: 4.83(at 25℃)
• Water Solubility: insoluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,3252
• BRN: 1424075
• CAS DataBase Reference: N,N-Dimethyl-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyl-1-naphthylamine(86-56-6)
• EPA Substance Registry System: N,N-Dimethyl-1-naphthylamine(86-56-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-51/53
• Safety Statements: 26-36-61-37/39-29
• RIDADR: UN 1369/2810
• WGK Germany: 2
• RTECS: QM2825000
• F: 8-9
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 86-56-6(Hazardous Substances Data)

Usage

Description

N,N-Dimethyl-1-naphthylamine is an organic compound with the chemical formula C12H13N. It is a light yellow liquid at room temperature and is known for its distinctive chemical properties.

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 this compound, 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

• 3282-30-2 pivaloyl chloride 
• 133071-22-4 [1-(dimethylamino)-8-naphthyl]lithium 
• 124-38-9 carbon dioxide 
• 2216-68-4 N-methylnaphthalen-1-amine 
• 134-32-7 1-amino-naphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 90-13-1 1-Chloronaphthalene 
• 67-56-1 methanol 
• 86-57-7 1-Nitronaphthalene 
• 2216-67-3 2-N-methylaminonaphthalene 
• 830-70-6 1-(N,N-dimethylamino)naphthalene-N-oxide 
• 64-18-6 formic acid 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 

Downstream Products

• 78062-03-0 4-Dimethylaminonaphthalene-1-carboxylic acid 
• 52912-75-1 dimethyl-[1]naphthyl-amine; compound with 1,3,5-trinitro-benzene 
• 195195-42-7 4-(4,4'-bis-dimethylamino-benzhydrylidene)-4H-naphthalen-1-one 
• 10433-94-0 N₁,N₁-dimethyl-5-nitronaphthalen-1-amine 
• 10273-29-7 1-dimethylamino-8-nitronaphthalene 
• 53663-33-5 N-(1-naphthyl)-N-methyl cyanamide 
• 34614-42-1 N⁴,N⁴,N^4',N^4'-tetramethyl-[1,1'-binaphthalene]-4,4'-diamine 
• 1971-81-9 4-dimethylamino-1-naphthaldehyde 
• 434955-69-8 (8-dimethylaminonaphth-1-yl)(methyl)(phenyl)phosphine 

Relevant articles and documents

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.

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).

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.