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

Chemical Properties

light yellow liquid

Uses

Different sources of media describe the Uses of 86-56-6 differently. You can refer to the following data:
1. Detection and determination of nitrites.
2. N,N-Dimethyl-1-naphthylamine is used in the nitrate reductase test to form a red precipitate of Prontosil by reacting with a nitrite-sulfanilic acid complex. And is also used to detection and determination of nitrites.

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

• 134-32-7 1-amino-naphthalene 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 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 
• 133071-22-4 [1-(dimethylamino)-8-naphthyl]lithium 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 552-46-5 1-naphthylamine hydrochloride 
• 7664-93-9 sulfuric acid 
• 1296794-22-3 N,N-dibenzyl-5-(dimethylamino)naphthalene-1-sulfonamide 

Downstream Products

• 78062-03-0 4-Dimethylaminonaphthalene-1-carboxylic acid 
• 52912-75-1 dimethyl-[1]naphthyl-amine; compound with 1,3,5-trinitro-benzene 
• 53663-33-5 N-(1-naphthyl)-N-methyl cyanamide 
• 7467-30-3 4-(4-dimethylamino-[1]naphthylazo)-benzenesulfonic acid 
• 202983-69-5 (4-dimethylamino-[1]naphthyl)-bis-(4-dimethylamino-phenyl)-methane 
• 861802-84-8 [4-(4-dimethylamino-benzhydryl)-[1]naphthyl]-dimethyl-amine 
• 10336-21-7 dimethyl-[4-(4-nitro-phenylazo)-[1]naphthyl]-amine 
• 10537-10-7 dimethyl-(4-phenylazo-[1]naphthyl)-amine 
• 4272-77-9 dansyl acid 
• 10273-29-7 1-dimethylamino-8-nitronaphthalene 
• 13541-35-0 1-N,N-dimethylamino-5,6,7,8-tetrahyfronaphthalene 
• 1971-81-9 4-dimethylamino-1-naphthaldehyde 
• 59557-93-6 4-bromo-1-(N,N-dimethylamino)naphthalene 
• 68582-46-7 bis-(4-dimethylamino-[1]naphthyl)-phenyl-methane 

Relevant articles and documents

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.

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.

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.