5416-11-5

Basic information

• Product Name: ETHYL (4-NITROPHENYLAMINO) OXOACETATE
• Synonyms: ETHYL (4-NITROPHENYLAMINO) OXOACETATE;2-[(4-Nitrophenyl)aMino]-2-oxo-acetic Acid Ethyl Ester;4'-Nitro-oxanilic Acid Ethyl Ester;N-(4-Nitrophenyl)oxaMic Acid Ethyl Ester;NSC 11343;NSC 55318;Oxalic Acid Monoethyl Ester N-(4-Nitrophenyl)aMide
• CAS NO: 5416-11-5
• Molecular Formula: C₁₀H₁₀N₂O₅
• Molecular Weight: 238.2
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 5416-11-5.mol

Chemical Properties

• Melting Point: 172-173°C
• Appearance: /
• Density: 1.394g/cm³
• Refractive Index: 1.595
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: ETHYL (4-NITROPHENYLAMINO) OXOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (4-NITROPHENYLAMINO) OXOACETATE(5416-11-5)
• EPA Substance Registry System: ETHYL (4-NITROPHENYLAMINO) OXOACETATE(5416-11-5)

Safety Data

• Hazardous Substances Data: 5416-11-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
ETHYL (4-NITROPHENYLAMINO) OXOACETATE is used as a synthetic intermediate for the production of various organic compounds. Its chemical properties make it a suitable candidate for use in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ETHYL (4-NITROPHENYLAMINO) OXOACETATE is used as a key building block for the development of new drugs. Its reactivity and structural diversity enable chemists to design and synthesize novel therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Industry:
ETHYL (4-NITROPHENYLAMINO) OXOACETATE is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique chemical properties allow for the creation of innovative molecules with enhanced pest control capabilities and reduced environmental impact.
Used in Specialty Chemicals:
In the specialty chemicals sector, ETHYL (4-NITROPHENYLAMINO) OXOACETATE is employed as a starting material for the synthesis of various high-value compounds, such as dyes, fragrances, and additives. Its versatility and reactivity contribute to the development of new products with improved performance and functionality.

InChI:InChI=1/C10H10N2O5/c1-2-17-10(14)9(13)11-7-3-5-8(6-4-7)12(15)16/h3-6H,2H2,1H3,(H,11,13)

Upstream product

• 100-01-6 4-nitro-aniline 
• 95-92-1 oxalic acid diethyl ester 
• 4755-77-5 Ethyl oxalyl chloride 
• 64-17-5 ethanol 
• 1457-85-8 Ethyl oxanilate 
• 7697-37-2 nitric acid 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 

Downstream Products

• 64-17-5 ethanol 
• 144-62-7 oxalic acid 
• 100-01-6 4-nitro-aniline 
• 67472-09-7 N-hydroxy-N'-(4-nitro-phenyl)-oxalamide 
• 41116-36-3 (4-nitro-phenyl)-oxalamide 
• 53117-24-1 (4-nitro-phenyl)-oxalamic acid hydrazide 
• 50341-51-0 N-(4-dimethylamino-phenyl)-N'-(4-nitro-phenyl)-oxalamide 
• 72304-33-7 N-(5-amino-[1,3,4]thiadiazole-2-sulfonyl)-N'-(4-nitro-phenyl)-oxalamide 
• 6432-59-3 Oxalsaeure-<4-nitro-anilid>-p-toluolsulfonylamid 
• 57864-89-8 1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-3-carboxylic acid 4-nitro-anilide 
• 97061-85-3 N'-<4-Diaethylamino-1-methyl-butyl>-N-<4-nitro-phenyl>-oxamid 
• 50341-49-6 N-(p-methoxyphenyl)-N'-(p-nitrophenyl)-oxalamide 
• 880150-44-7 N¹-benzyl-N²-(4-nitrophenyl)ethanediamide 

Relevant articles and documents

New N-phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATPase inhibitors of DNA gyrase

Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 μM against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds - especially by varying their size, the position and orientation of key functional groups, and their acid-base properties. The structure-activity relationship (SAR) was examined and the results were rationalised with molecular docking.

A transformation of N-alkylated anilines to N-aryloxamates

Transformation of N-alkylated anilines to N-aryloxamates was studied using ethyl 2-diazoacetoacetate as an alkylating agent and dirhodium tetraacetate (Rh2(OAc)4) as the catalyst. The general applicability of the reaction as a synthetic method for N-aryloxamates was studied with a number of substituted N-alkylated anilines. The results revealed that the oxamate was formed by a radical reaction with molecular O2 and Rh 2(OAc)4 as initiator. Copyright

New Highlights in the Synthesis of 4-Aryl-1,4-dihydropyrazines

The 4-aryl-1,4-dihydropyrazines were prepared via the cyclization of N,N-bisalkylated anilines with ammonium acetate. These reactions were aided by improvements in the synthesis of N,N-bisalkylated anilines which were alkylated with anilines using ethyl 2-diazo acetoacetate in a reaction catalyzed by rhodium acetate in the absence of oxygen. A possible mechanistic route is postulated on the basis of the isolation of the N-alkylation intermediates, which were determined to be N-aryloxamates by 1H NMR data and X-ray diffraction.

2- [ (2-SUBSTITUTED) -IND0LIZIN-3-YL] -2-OXO-ACETAMIDE DERIVATIVES AS ANTIFUNGAL AGENTS

The invention provides compounds of formula (I), and pharmaceutically acceptable salts thereof wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. These compounds are useful in the manufacture of medicaments for use in the prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.

Synthesis of unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and bis(quinazolin-4-on-2-yls) by double-anion-capture reactions of unsymmetrical oxaldi(arylimidoyl) dichlorides

Unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and bis(quinazolin-4-on-2- yls) were prepared by one-pot cyclisations of unsymmetrical oxaldi(arylimidoyl) dichlorides. Georg Thieme Verlag Stuttgart.

Chemical hybridizing agents for chickpea (Cicer arietinum L.): Leads from QSAR analysis of ethyl oxanilates and pyridones

In the self-pollinated crops such as chickpea, induction of male sterility by deployment of chemical hybridizing agents (CHAs) facilitating "two-line" approach holds immense potential in heterosis breeding. A total of 40 test CHAs comprising 20 ethyl oxanilates and 20 pyridones were screened as potential CHAs on chickpea (variety BG 1088) at 500, 800, and 1000 ppm. Three test compounds mostly having either F (4)/Br (5)/CF3 (19) at the para position of the aryl ring from a pool of 20 ethyl oxanilates were identified as the most potent CHAs causing >99% induction of pollen sterility and >90% total flower sterility at 1000-ppm test concentration. Among pyridone derivatives, N-(4-chlorophenyl)-5-carbethoxy-4,6-dimethyl, 1,2-dihydropyrid-2-one (26) was found to be the most active. Quantitative structure activity relationship (QSAR) analysis has revealed a direct involvement of Swain-Lupton field constant, Fp, with the target bioactivity which implied that field rather than resonance effect (R) had a positive effect on the activity. The real guiding principle for selectivity was found out to be the hydrophobic parameter π value. The QSAR models indicated that increased steric bulk at the 4-position on the phenyl ring is associated with enhanced activity. The CHAs appeared to act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by premature callase secretion.

Synthesis of unsymmetrical bis(imidoyl)dichlorides of oxalic acid

Unsymmetrical oxalic acid-bis(imidoyl)dichlorides were prepared from ethyl 2-chloro-2-oxoacetate in three steps.

Synthesis of 2-(arylamino)-2-(arylimino)acetamides

The reaction of 2-(arylamino)-2-oxoacetates with PCl5 afforded 2-(arylamino)-2,2-dichloroacetates. The reaction of these compounds with aniline derivatives allowed a convenient synthesis of a great variety of 2-(arylamino)-2-(arylimino)acetamides. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of Unsymmetrical Pyrrolo[3,2-b]pyrrole-2,5-diones

The first unsymmetrical oxalic acid-bis(imidoyl)dichlorides were prepared and applied to the one-pot synthesis of the first unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and 2,2′-bis-quinazolin-4-ones.

Synthesis and quantitative structure-activity relationships of oxanilates as chemical hybridizing agents for wheat (Triticum aestivum L.)

Chemical hybridizing agents (CHAs) can facilitate two-line breeding in heterosis programs of crops. Twenty-seven oxanilates having different aromatic substitutions were synthesized and screened as CHAs on two genotypes of wheat, PBW 343 and HD 2733, during two Rabi (winter) seasons, 2000-01 and 2001-02. The oxanilates prepared by thermal condensation of anilines with diethyl oxalate or by acylation with ethoxycarbonyl methanoyl chloride were sprayed at 1000 and 1500 ppm at the premeiotic stage of wheat, when the length of the emerging spike of the first node was 7-8 mm. Pollen sterility and spikelet sterility were measured in each treatment. Ethyl oxanilates 5, 6, and 25, containing 4-F, 4-Br, and 4-CF3 aromatic substituents, respectively, induced greater than 98% spikelet sterility, the desired level, at 1500 ppm. Quantitative structure-activity relationship analysis revealed a direct relationship between Fp and molecular mass but an inverse relationship between MR, Es, and R in influencing the bioactivity. Several F1 hybrids were developed using 5, and at least one showed heterosis.