6330-55-8

Basic information

• Product Name: N-methyl-N-nitrosonaphthalen-2-amine
• CAS NO: 6330-55-8
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.2099
• Mol File: 6330-55-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 366.5°C at 760 mmHg
• Flash Point: 175.4°C
• Density: 1.13g/cm³
• Vapor Pressure: 1.46E-05mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: N-methyl-N-nitrosonaphthalen-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-N-nitrosonaphthalen-2-amine(6330-55-8)
• EPA Substance Registry System: N-methyl-N-nitrosonaphthalen-2-amine(6330-55-8)

Safety Data

• Hazardous Substances Data: 6330-55-8(Hazardous Substances Data)

Upstream product

• 580-13-2 2-bromonaphthalene 
• 74-88-4 methyl iodide 
• 2216-67-3 2-N-methylaminonaphthalene 

Downstream Products

• 40300-36-5 methyl-(1-phenylazo-[2]naphthyl)-amine 

Relevant articles and documents

One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives

The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.

Cp?Rh(iii) catalyzed: Ortho -halogenation of N -nitrosoanilines by solvent-controlled regioselective C-H functionalization

We present a novel, efficient, and regioselective method for the rhodium-catalyzed direct C-H ortho-halogenation of anilines that involves a removable N-nitroso directing group. This method featured mild reaction conditions, wide substrate scope, good functional group tolerance and satisfactory yields. To maintain the high ortho-regioselectivity and conversion, increasing the steric hindrance of the solvent was critical. Preliminary mechanistic studies suggest that C-H activation may be involved in the rate-determining step.

Rhodium(III)-Catalyzed Directed C?H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles

An efficient rhodium-catalyzed direct C?H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.