17485-25-5

Basic information

• Product Name: N,3-dimethyl-N-nitrosoaniline
• CAS NO: 17485-25-5
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.1778
• Mol File: 17485-25-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 288.9°C at 760 mmHg
• Flash Point: 128.5°C
• Density: 1.04g/cm³
• Vapor Pressure: 0.00228mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: N,3-dimethyl-N-nitrosoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,3-dimethyl-N-nitrosoaniline(17485-25-5)
• EPA Substance Registry System: N,3-dimethyl-N-nitrosoaniline(17485-25-5)

Safety Data

• Hazardous Substances Data: 17485-25-5(Hazardous Substances Data)

Upstream product

• 121-72-2 N,N-dimethyl-m-toluidine 
• 509-14-8 tetranitromethane 
• 696-44-6 N-methyl-m-toluidine 
• 110-46-3 isopentyl nitrite 
• 108-44-1 1-amino-3-methylbenzene 
• 39970-42-8 N-methyl-N-(3-methylphenyl)carboxamide 
• 110-86-1 pyridine 
• 64-17-5 ethanol 

Downstream Products

• 76570-59-7 4-methyl-2-(methylamino)phenol 
• 1610871-11-8 1,6-dimethyl-2,3-diphenyl-1H-indole 
• 78386-74-0 1,3,6-trimethyl-2-phenyl-1H-indole 
• 51786-43-7 N-(2,5-dimethylphenyl)-N-methylnitrous amide 
• 30427-10-2 2-methoxy-N,5-dimethylbenzenamine 

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.

Rhodium-catalyzed tandem acylmethylation/annulation ofN-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazoleN-oxides

An atom-economical protocol for synthesizing indazoleN-oxides from readily availableN-nitrosoanilines and sulfoxonium ylides through the rhodium(iii)-catalyzed C-H activation and cyclization reaction is described here. This protocol employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate to good yields under an ambient atmosphere, providing a straightforward approach to access structurally diverse and valuable indazoleN-oxide derivatives. Importantly, this new annulation process represents a hitherto unobserved reactivity pattern for theN-nitroso group.

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.