24171-80-0

Basic information

• Product Name: Benzenamine, N-hydroxy-3-methoxy-
• CAS NO: 24171-80-0
• Molecular Formula: C7H9NO2
• Molecular Weight: 139.154
• Mol File: 24171-80-0.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-hydroxy-3-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-hydroxy-3-methoxy-(24171-80-0)
• EPA Substance Registry System: Benzenamine, N-hydroxy-3-methoxy-(24171-80-0)

Safety Data

• Hazardous Substances Data: 24171-80-0(Hazardous Substances Data)

Upstream product

• 70-18-8 GLUTATHIONE 
• 536-90-3 m-Anisidine 
• 555-03-3 3-nitroanisole 

Downstream Products

• 210224-49-0 2-(3-Methoxy-phenyl)-4-phenyl-2H-isoxazol-5-one 
• 23084-35-7 2-(6-methoxy-1H-indol-3-yl)acetonitrile 
• 103986-22-7 2-(6-methoxy-1H-indol-3-yl)acetic acid 
• 131424-27-6 methyl 6-methoxy-1H-indole-3-carboxylate 
• 131424-26-5 1-benzyl 3-methyl 6-methoxyindole-1,3-dicarboxylate 
• 123380-87-0 6-methoxy-1H-indole-3-acetic acid methyl ester 
• 140862-48-2 (6-methoxyindol-3-yl)methanol 
• 161532-19-0 methyl 4-methoxy-1H-indole-3-carboxylate 
• 613679-11-1 (6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone 
• 131424-25-4 benzyl N-hydroxy-n-(3-methoxyphenyl)carbamate 
• 112667-99-9 N-m-methoxyphenyl-2-furylacrylohydroxamic acid 

Relevant articles and documents

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration

The one-pot two-step intramolecular aryl and heteroaryl C-H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N-OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.