937-25-7

Basic information

• Product Name: N-nitroso-N-methyl-4-fluoroaniline
• Synonyms: N-nitroso-N-methyl-4-fluoroaniline
• CAS NO: 937-25-7
• Molecular Formula: C₇H₇FN₂O
• Molecular Weight: 154.16
• Mol File: 937-25-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 104°C (rough estimate)
• Flash Point: 118.1°C
• Appearance: /
• Density: 1.2456 (estimate)
• Vapor Pressure: 0.00636mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: N-nitroso-N-methyl-4-fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-nitroso-N-methyl-4-fluoroaniline(937-25-7)
• EPA Substance Registry System: N-nitroso-N-methyl-4-fluoroaniline(937-25-7)

Safety Data

• Hazardous Substances Data: 937-25-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H7FN2O/c1-10(9-11)7-4-2-6(8)3-5-7/h2-5H,1H3

Upstream product

• 459-59-6 4-fluoro-N-methylaniline 

Downstream Products

• 41192-31-8 5-fluoro-2,3-dihydro-1-methylindol-2-one 
• 388078-34-0 1-methyl-5-fluoroindoline 
• 388078-30-6 2-chloro-N-(4-fluorophenyl)-N-methylacetamide 
• 1416897-79-4 (E)-methyl 3-(5-fluoro-2-(methylamino)phenyl)acrylate 
• 1416897-53-4 (E)-methyl 3-(5-fluoro-2-(methyl(nitroso)amino)phenyl)acrylate 
• 1042987-87-0 5-fluoro-1-methyl-3-phenyl-1H-indazole 
• 39573-21-2 (5-fluoro-2-(methylamino)phenyl)(phenyl)methanone 
• 1446319-69-2 5-fluoro-1,3-dimethyl-2-phenyl-1H-indole 

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.

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.