304-88-1

Basic information

• Product Name: N-Phenylbenzohydroxamic acid
• Synonyms: Benzamide, N-hydroxy-N-phenyl-;Benzohydroxamic acid, N-phenyl-;BPHA;N-Benzoyl-N-phenylhydroxamic acid;N-Benzoyl-N-phenylhydroxylamin;N-Hydroxybenzanilide;n-hydroxy-n-phenyl-benzamid;N-Phenylbenzohyroxamic acid
• CAS NO: 304-88-1
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23
• EINECS: 206-158-9
• Product Categories: Analytical Chemistry;Bipyridyls, etc. (Chelating Reagents);Chelating Reagents;Hydroxylamines;Hydroxylamines (N-Substituted);Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 304-88-1.mol

Chemical Properties

• Melting Point: 118-120 °C(lit.)
• Boiling Point: 353.22°C (rough estimate)
• Flash Point: 177.1 °C
• Appearance: Light beige needle-like/Needle-Like Crystals or Crystalline Powder
• Density: 1.1544 (rough estimate)
• Vapor Pressure: 4.19E-06mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• PKA: 8.09±0.19(Predicted)
• Water Solubility: Practically insoluble in water
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 2212449
• CAS DataBase Reference: N-Phenylbenzohydroxamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenylbenzohydroxamic acid(304-88-1)
• EPA Substance Registry System: N-Phenylbenzohydroxamic acid(304-88-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 304-88-1(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
N-Phenylbenzohydroxamic acid is used as a complexing agent for studying the dispersive liquid-liquid microextraction based on solidification of floating organic drop (DLLME-SFO) behavior of vanadium (V). It plays a crucial role in the extraction and analysis of vanadium, a critical element in various industrial applications.
Used in Environmental Analysis:
N-Phenylbenzohydroxamic acid is used as an extractant in the determination of beryllium in natural waters. Beryllium is a toxic element that can pose health risks if present in high concentrations, making its detection and quantification essential for environmental monitoring and protection.

Purification Methods

Recrystallise it from hot water, *benzene Et2O/hexane or acetic acid. It complexes with metals. [Beilstein 15 III 8, 15 IV 7.]

InChI:InChI=1/C13H11NO2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,16H

Upstream product

• 16817-95-1 N-benzoyl-N-phenyl-O-(benzoyl)hydroxylamine 
• 100-52-7 benzaldehyde 
• 98-95-3 nitrobenzene 
• 98-88-4 benzoyl chloride 
• 100-65-2 N-Phenylhydroxylamine 
• 60-29-7 diethyl ether 
• 93-97-0 benzoic acid anhydride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 586-96-9 Nitrosobenzene 
• 611-73-4 Benzoylformic acid 
• 84447-15-4 phenylhydroxylamine oxalate 
• 54245-99-7 N-phenyl-N-benzoyl-O-methylhydroxylamine 
• 128-08-5 N-Bromosuccinimide 
• 201024-81-9 C,N-diphenylnitrone 

Downstream Products

• 93-98-1 N-phenyl benzoyl amide 
• 54245-99-7 N-phenyl-N-benzoyl-O-methylhydroxylamine 
• 19958-58-8 N-benzoyl-N-phenyl-O-(acetyl)hydroxylamine 
• 776-75-0 N-benzoylpiperidine 
• 110875-78-0 N-Phenyl-N-phenylacetoxy-benzamide 
• 135308-25-7 N-Diphenylacetoxy-N-phenyl-benzamide 
• 135308-26-8 N-Phenyl-N-(2-phenylsulfanyl-acetoxy)-benzamide 
• 73153-57-8 2-Benzamidophenyl-cyclohexansulfonat 
• 73153-53-4 4-Benzamidophenyl-cyclohexyl-sulfon 
• 73153-50-1 (2-Benzamidophenyl)-cyclohexyl-sulfon 
• 83142-14-7 C₁₄H₁₃NO₄S 
• 112308-00-6 N-benzoyl-S-dimethylcarbamoyl-N-phenylhydroxylamine 
• 112308-02-8 N-benzoyl-S-dimethylcarbamoyl-o-aminothiophenol 
• 91827-26-8 N-benzoyl-S-dimethylcarbamoyl-p-aminothiophenol 

Relevant articles and documents

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Concerted [1,3]-Rearrangement in Cationic Cobalt-Catalyzed Reaction of O-(Alkoxycarbonyl)-N-arylhydroxylamines

O-(Alkoxycarbonyl)-N-arylhydroxylamines were efficiently converted to 2-aminophenol derivatives by cationic cobalt catalysts at 30 °C. The results of 18O-labeling experiments suggested that rearrangement of the alkoxycarbonyl group from the aniline nitrogen to the ortho position proceeded in an unprecedented [1,3] manner.

Copper-Catalyzed Aerobic Decarboxylation/Ketooxygenation of Electron-Deficient Alkenes

A copper-catalyzed ketooxygenation of electron-deficient alkenes was developed. This approach combines O-H alkylation, aerobic decarboxylation, and oxygenation in one transformation. Mechanistic investigation of this reaction showed that the copper salt is responsible for both generating the amidoxyl radical and promoting aerobic decarboxylation.

N-heterocyclic-carbene-catalyzed one-pot synthesis of hydroxamic esters

The honey pot: The NHC-catalyzed reaction between nitrosobenzenes, aromatic/aliphatic aldehydes, and enals proceeded through an aza-benzoin-type reaction and an internal redox esterification to afford hydroxamic esters in good yields. Copyright

Solid-phase extraction of plutonium(IV) an americium(III) using N-benzoylphenylhydroxylamine and its derivatives

The recovery and separation of plutonium(IV) and americium(III) by solid-phase extraction (SPE) on alkylated silica gel S16 modified with N-benzoylphenylhydroxylamine (BPHA) and with its derivatives was studied. BPHA was modified by introducing into the p-position of the phenyl ring of electronactive substituents that differ in their hydrophobicity: CH3, Ph, Cl, F, and NO2. The SPE of plutonium(IV) and americium(III) was studied in the range of acidities from pH 8 to 1 M HNO3. The recovery and separation of these elements was shown to depend on the nature of the substituent, aqueous acidity, and the preparation of S16 to SPE experiments.

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.

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.

Asymmetric synthesis of N-aryl aziridines

The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer's sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer's auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantioselection and a mechanism is proposed for the aziridination reaction.

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.