13664-49-8

Basic information

• Product Name: N-HYDROXY-4-METHOXY-N-PHENYL-BENZAMIDE
• Synonyms: N-HYDROXY-4-METHOXY-N-PHENYL-BENZAMIDE;4-METHOXY-N-PHENYLBENZOHYDROXAMIC ACID
• CAS NO: 13664-49-8
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.26
• Mol File: 13664-49-8.mol

Chemical Properties

• Melting Point: 113 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 420.2°C at 760 mmHg
• Flash Point: 208°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 8.18E-08mmHg at 25°C
• Refractive Index: 1.639
• PKA: 8.22±0.19(Predicted)
• CAS DataBase Reference: N-HYDROXY-4-METHOXY-N-PHENYL-BENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-HYDROXY-4-METHOXY-N-PHENYL-BENZAMIDE(13664-49-8)
• EPA Substance Registry System: N-HYDROXY-4-METHOXY-N-PHENYL-BENZAMIDE(13664-49-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13664-49-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13NO3/c1-18-13-9-7-11(8-10-13)14(16)15(17)12-5-3-2-4-6-12/h2-10,17H,1H3

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 119-52-8 4,4'-dimethoxybenzoin 
• 586-96-9 Nitrosobenzene 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 100-65-2 N-Phenylhydroxylamine 
• 100-09-4 4-methoxybenzoic acid 
• 586-96-9 Nitrosobenzene 
• 84927-87-7 MoO₂(ON(C₆H₅)CO(C₆H₄OCH₃))2 
• 1445871-83-9 C₂₀H₂₁NO₃ 
• 1445871-98-6 C₂₀H₂₁NO₃ 
• 23600-48-8 N-(4-hydroxyphenyl)-4-methoxybenzamide 
• 1309926-82-6 O-(4-methylbenzoyl)-N-phenyl-4-methoxybenzohydroxamic acid 
• 7465-88-5 4-methoxy-N-phenylbenzamide 

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.

Interrupted fischer-indole intermediates via oxyarylation of alkenyl boronic acids

The oxyarylation of alkenyl boronic acids with N-arylbenzhydroxamic acids has been achieved under both copper-mediated and copper-catalyzed conditions to provide access to interrupted Fischer-indole intermediates. This transformation is believed to proceed through a copper-promoted C-O bond forming event followed by a [3,3] rearrangement. The scope of the method is described and mechanistic experiments are discussed.

Photoacid generators (PAGs) based on N-acyl-N-phenylhydroxylamines for carboxylic and sulfonic acids

Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-acyl-N-phenylhydroxylamines have been demonstrated. Irradiation of o-carboxylates and thermally rearranged o-arenesulfonates of N-acyl-N-phenylhydroxylamines using UV light (≥254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of N-acyl-N- phenylhydroxylamines was found to be dependent on their N-acyl substituents. Further, polymer bearing o-arenesulfonates of N-acyl-N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids.

Benzaldehyde lyase-catalyzed direct amidation of aldehydes with nitroso compounds

Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with nitroso compounds and furnishes N-arylhydroxamic acids in high yields. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to their reaction with nitroso compounds. The kinetic resolution of rac-2-hydroxy-1,2-diphenylethanones furnished (S)-benzoins and arylhydroxamic acids with high enantioselectivities and conversions.

Laccase Variants

The present invention relates to variants of a parent laccase. The present invention also relates to polynucleotides encoding the variant laccases and to nucleic acid constructs, vectors, and host cells comprising the polynucleotides, and methods of using the variant enzymes.

N-HETEROCYCLIC CARBENE (NHC) CATALYZED SYNTHESIS OF HYDROXAMIC ACIDS

A process for preparing hydroxamic acids is provided. The process comprises reacting an aldehyde with a nitroso compound in the presence of a N-heterocyclic carbene (NHC) catalyst.

N-heterocyclic carbene (NHC)-catalyzed direct amidation of aldehydes with nitroso compounds

(Chemical Equation Presented) NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of α-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.

ANTIMICROBIAL COMPOSITION CONTAINING AN OXIDOREDUCTASE AND AN ENHANCER OF THER N-HYDROXYANILIDE-TYPE

The present invention relates to an enzymatic composition capable of killing or inhibiting microbial cells or micro-organisms, e.g. in laundry, on hard surfaces, in water systems, on skin, on teeth or on mucous membranes. The present invention also relate

Substituent effects in the micellar hydrolysis of N-phenylbenzohydroxamic acid under acidic conditions

The rates of hydrolysis of some para-substituted N-phenylbenzohydroxamic acids (X.C6H4.(C = O).N(OH)C6H5; X = H, CH3, OCH3, F, NO2) under acidic conditions with cationic, anionic and nonionic surfactants have been measured. Substituent effects upon first order rate constants in water and at the micellar surface fitted Hammett equation, based on σ, σ+, σ- parameters. Values of 'p' increase with increasing surfactant concentration. The substituent effects indicate specific micellar influences on the rates and a difference in mechanism between the bulk aqueous phase and the micellar phase. The lipophilicity and polar effects of the substituents have also been evaluated.