2436-85-3

Basic information

• Product Name: N,N-DIMETHYL-2-NAPHTHYLAMINE
• Synonyms: 2-DIMETHYLAMINONAPHTHALENE;N,N-DIMETHYL-2-NAPHTHYLAMINE;2-Naphthalenamine, N,N-dimethyl-;dimethyl(2-naphthyl)amine;N,N-Dimethyl-2-naphthalenamine;N,N-dimethyl-naphthalen-2-yl-amine;2-Naphtyldimethylamine;N,N-Dimethyl-2-naphtylamine
• CAS NO: 2436-85-3
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• EINECS: 219-432-8
• Mol File: 2436-85-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 46 °C
• Boiling Point: 305 °C
• Flash Point: 123.4°C
• Appearance: /
• Density: 1.0279
• Vapor Pressure: 0.000948mmHg at 25°C
• Refractive Index: 1.6443
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.566(at 25℃)
• CAS DataBase Reference: N,N-DIMETHYL-2-NAPHTHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-2-NAPHTHYLAMINE(2436-85-3)
• EPA Substance Registry System: N,N-DIMETHYL-2-NAPHTHYLAMINE(2436-85-3)

Safety Data

• Hazardous Substances Data: 2436-85-3(Hazardous Substances Data)

Usage

Uses

N,N-Dimethyl-2-naphthylamine is a useful chemical in organic synthesis.

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

Upstream product

• 512-56-1 trimethyl phosphite 
• 91-59-8 naphthalen-2-ylamine 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 612-52-2 2-naphthylamine hydrochloride 
• 124-40-3 dimethyl amine 
• 135-19-3 β-naphthol 
• 77-78-1 dimethyl sulfate 
• 53952-98-0 2-(prop-2′-ynyl)benzaldehyde 
• 580-13-2 2-bromonaphthalene 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 91-58-7 2-chloronaphthalene 
• 108-88-3 toluene 

Downstream Products

• 4942-77-2 N-methyl-N-(naphthalen-2-yl)benzamide 
• 787-84-8 N'-benzoylbenzohydrazide 
• 6945-44-4 JGC 139 
• 13541-31-6 dimethyl-(5,6,7,8-tetrahydro-[2]naphthyl)-amine 
• 135029-77-5 (R)-N,N,N',N'-tetramethyl-<1,1'-binaphthalene>-2,2'-diamine 
• 91-20-3 naphthalene 
• 93-04-9 2-Methoxynaphthalene 

Relevant articles and documents

Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes

A series of 4-substituted-1,2-diethylnylbenzenes were prepared (1a-f) and subjected to Bergman cyclization. Bulk cyclization proceeded to produce the corresponding 2-substituted naphthalenes (2a-f) in good yields (59-78%). Kinetic experiments show a linear free energy relationship between the cyclization rate and the Hammett σ(m) substituent coefficient and the Swain-Lupton field and resonance parameters. (C) 2000 Elsevier Science Ltd.

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.

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.