4546-20-7

Basic information

• Product Name: Benzenamine, N-hydroxy-4-methoxy-
• CAS NO: 4546-20-7
• Molecular Formula: C7H9NO2
• Molecular Weight: 139.154
• Mol File: 4546-20-7.mol
• Article Data: 38

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-hydroxy-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-hydroxy-4-methoxy-(4546-20-7)
• EPA Substance Registry System: Benzenamine, N-hydroxy-4-methoxy-(4546-20-7)

Safety Data

• Hazardous Substances Data: 4546-20-7(Hazardous Substances Data)

Upstream product

• 100-17-4 para-methoxynitrobenzene 
• 104-94-9 4-methoxy-aniline 
• 66682-84-6 N-(4-Methoxyphenyl)acetohydroxamsaeure 
• 1516-21-8 4-methoxynitrosobenzene 
• 124-40-3 dimethyl amine 

Downstream Products

• 1562-94-3 4,4'-azoxy anisole 
• 3170-90-9 2-(N-hydroxy-4-methoxy-anilino)-benzo[e][1,3]oxazin-4-one 
• 909725-91-3 N-[(diisopropylcarbamoyl)methylene]-4-methoxyaniline N-oxide 
• 3170-88-5 Iminokohlensaeure-(2,2,2-trichlor-ethylester)-(4-methoxy-phenylhydroxylamid) 
• 35684-20-9 C₁₈H₂₁NO₂ 
• 3170-89-6 C₂₂H₂₂N₄O₆ 
• 172595-68-5 methyl 5-methoxy-1H-indole-3-carboxylate 
• 51335-08-1 (4-methoxy-phenylimino)-phenyl-acetic acid methyl ester 
• 1562-94-3 4,4'-dimethoxyazoxybenzene 
• 3585-93-1 N-(4-methoxybenzylidene)aniline oxide 
• 1445871-72-6 N-(pentafluorobenzoyl)-N-(p-OMe-phenyl)hydroxylamine 
• 1445871-86-2 C₁₈H₁₄F₅NO₃ 
• 1426845-70-6 8-[acetyl(4-methoxyphenyl)amino]-2'-deoxyguanosine 
• 1426845-67-1 8-[acetyl(4-methoxyphenyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 

Relevant articles and documents

α-Effect Menschutkin alkylations

The Menschutkin-type alkylation of substituted N-methylanilines with methyl arenesulfonates is compared to the same reaction with substituted N- phenylhydroxylamines. The α-effects are small but measurable. The Hammett ρ parameters are not useful in this reaction series as an index of transition- state character. The use of β(1g)(Me) parameters along with β(nuc) values allows the transition states to be placed on the energy surface. The pattern is that the α-nucleophiles form tighter transition states than the normal nucleophiles. The size of the α-effect is related to the ionization potentials (IPs) computed by the AM1 Hamiltonian for a wide variety of reactions showing the α-effect. The larger α-effects depend more greatly on the IP.

Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes

A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.

Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines

We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.