1613-76-9

Basic information

• Product Name: N-hydroxy-4-nitrobenzamide
• Synonyms: N-hydroxy-4-nitrobenzamide;4-Nitrobenzeneformhydroxamic acid;4-Nitrobenzohydroxamic acid;4-Nitrobenzohydroximic acid;p-Nitrobenzohydroxamic acid
• CAS NO: 1613-76-9
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.1335
• Mol File: 1613-76-9.mol
• Article Data: 29

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.485g/cm³
• Refractive Index: 1.624
• CAS DataBase Reference: N-hydroxy-4-nitrobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-4-nitrobenzamide(1613-76-9)
• EPA Substance Registry System: N-hydroxy-4-nitrobenzamide(1613-76-9)

Safety Data

• Hazardous Substances Data: 1613-76-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H6N2O4/c10-7(8-11)5-1-3-6(4-2-5)9(12)13/h1-4,11H,(H,8,10)

Upstream product

• 99-77-4 ethyl 4-nitrobenzoate 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 57139-18-1 potassium p-nitrobenzohydroxyamate 
• 555-16-8 4-nitrobenzaldehdye 
• 30364-58-0 p-nitrobenzoic acid N-hydroxysuccinimide ester 
• 619-73-8 4-nitrobenzyl chloride 
• 15568-73-7 5,5-dimethyl-3-(p-nitrophenyl)-1,4,2-dioxazole 
• 62-23-7 4-nitro-benzoic acid 
• 122-04-3 4-nitro-benzoyl chloride 
• 1037-31-6 4-nitrophenyl 4-nitrobenzoate 

Downstream Products

• 2290-01-9 3-(4-nitro-phenyl)-1,4-dioxa-2-aza-spiro[4.5]dec-2-ene 
• 66437-43-2 1-[3-(4-nitro-phenyl)-[1,4,2]dioxazol-5-yl]-propan-2-one 
• 99-77-4 ethyl 4-nitrobenzoate 
• 15568-73-7 5,5-dimethyl-3-(p-nitrophenyl)-1,4,2-dioxazole 
• 1036388-89-2 C₁₇H₂₆N₄O₄ 
• 1036388-70-1 C₁₇H₂₆N₄O₄ 
• 100-01-6 4-nitro-aniline 
• 968-08-1 O-Benzoyl-p-nitrobenzohydroxamic acid 
• 26071-05-6 4-aminobenzohydroxamic acid 
• 54225-73-9 N-(4-nitro-benzoyl)-O-(4-nitro-phenylcarbamoyl)-hydroxylamine 
• 80-05-7 BPA 
• 16063-05-1 2-(4-nitrophenyl)-4H-3,1-benzoxazin-4-one 
• 587-90-6 bis-N,N'-(4-nitrophenyl)urea 
• 1418203-46-9 5-(4-nitrophenyl)imidazo[1,2-c]quinazoline 

Relevant articles and documents

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones

A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr).

Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides

The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.

Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions

The acyl nitroso Diels–Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro-induced decomposition could be suppressed in favour of the 1,2-oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3-dienes and hydroxamic acids, giving up to 96 % isolated yield.