17405-06-0

Basic information

• Product Name: 3-bromo-N-methyl-N-nitrosoaniline
• CAS NO: 17405-06-0
• Molecular Formula: C₇H₇BrN₂O
• Molecular Weight: 215.0473
• Mol File: 17405-06-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 325.9°C at 760 mmHg
• Flash Point: 150.9°C
• Density: 1.52g/cm³
• Vapor Pressure: 0.000223mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 3-bromo-N-methyl-N-nitrosoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-N-methyl-N-nitrosoaniline(17405-06-0)
• EPA Substance Registry System: 3-bromo-N-methyl-N-nitrosoaniline(17405-06-0)

Safety Data

• Hazardous Substances Data: 17405-06-0(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 64-17-5 ethanol 
• 509-14-8 tetranitromethane 
• 16518-62-0 3-bromo-N,N-dimethylaniline 
• 66584-32-5 3-bromo-N-methylaniline 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 1416897-61-4 (E)-methyl 3-(2-bromo-6-(methyl(nitroso)amino)phenyl)acrylate 
• 1416897-62-5 (E)-methyl 3-(4-bromo-2-(methyl(nitroso)amino)phenyl)acrylate 
• 1416897-87-4 (E)-methyl 3-(2-bromo-6-(methylamino)phenyl)acrylate 
• 1416897-88-5 (E)-methyl 3-(4-bromo-2-(methylamino)phenyl)acrylate 
• 848750-28-7 4-bromo-1,3-dimethyl-2-phenyl-1H-indole 
• 1226985-36-9 6-bromo-1-methyl-1H-indazol-3-ol 
• 90084-67-6 1-(3-Bromophenyl)-1-methylhydrazine 

Relevant articles and documents

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.

Rhodium-catalyzed oxidative C-H/C-H cross-coupling of aniline with heteroarene: N-nitroso group enabled mild conditions

The development of transition metal-catalyzed oxidative C-H/C-H cross-coupling between two (hetero)arenes to forge aryl-heteroaryl motifs under mild conditions is an appealing yet challenging task. Herein, we disclose a rhodium-catalyzed oxidative C-H/C-H cross-coupling reaction of an N-nitrosoaniline with a heteroarene under mild conditions. The judicious choice of the N-nitroso group as a directing group enables heightened reactivity. The coupled products could be transformed expediently to (2-aminophenyl)heteroaryl skeletons.