4835-39-6

Basic information

• Product Name: 4'-nitroacetoacetanilide
• Synonyms: 4'-nitroacetoacetanilide;ACETOACET-P-NITROANILIDE;ACETOACETAMINO-P-NITROANILIDE;Acetoacet-4-nitroanilide;N-(4-Nitrophenyl)-3-oxobutanamide;N-(4-Nitrophenyl)-3-oxobutyramide;3-keto-N-(4-nitrophenyl)butyramide;N-(4-Nitrophenyl)-3-oxobutyramide
• CAS NO: 4835-39-6
• Molecular Formula: C₁₀H₁₀N₂O₄
• Molecular Weight: 222.1974
• EINECS: 225-418-2
• Mol File: 4835-39-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 119.0 to 124.0 °C
• Boiling Point: 498.6 °C at 760 mmHg
• Flash Point: 255.3 °C
• Appearance: /
• Density: 1.331 g/cm³
• Storage Temp.: 2-8°C
• PKA: 10.59±0.46(Predicted)
• CAS DataBase Reference: 4'-nitroacetoacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-nitroacetoacetanilide(4835-39-6)
• EPA Substance Registry System: 4'-nitroacetoacetanilide(4835-39-6)

Safety Data

• Hazardous Substances Data: 4835-39-6(Hazardous Substances Data)

Usage

Chemical Properties

Bright yellow crystalline powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2431, 1985 DOI: 10.1021/jo00214a006

Upstream product

• 102-01-2 N-phenylacetoacetamide 
• 1694-31-1 tert-butyl acetoacetate 
• 100-01-6 4-nitro-aniline 
• 2537-98-6 C₁₆H₁₄N₄O₅ 
• 7647-01-0 hydrogenchloride 
• 2537-98-6 3-(4-nitro-anilino)-crotonic acid-(4-nitro-anilide) 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 
• 100-25-4 para-dinitrobenzene 

Downstream Products

• 93010-04-9 (2-Hydroxy-5-sulfamoyl-phenylazo)-4-nitro-acetoacetanilid 
• 83999-01-3 C₁₆H₁₂N₅O₁₀^(1-)*C₆H₁₅N*H⁽¹⁺⁾ 
• 880495-54-5 2,6-dimethyl-4-(4-hydroxyphenyl)-N,N'-bis-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxamide 
• 1258407-72-5 N-(4-nitrophenyl)-4-(furan-2-yl)-2-methyl-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxamide 
• 1258407-63-4 4-(thiophen-2-yl)-6-methyl-N-(4-nitrophenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1258407-55-4 4-phenyl-6-methyl-N-(4-nitrophenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1373441-69-0 1,2,3,4-tetrahydro-6-methyl-N-(4-nitrophenyl)-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxamide 
• 1373441-68-9 1,2,3,4-tetrahydro-6-methyl-N-(4-nitrophenyl)-2-oxo-4-(1,3-diphenyl-1H-pyrazol-4-yl)pyrimidine-5-carboxamide 
• 1448062-56-3 2,6-dimethyl-N,N'-bis-(4-nitrophenyl)-4-(p-tolyl)-1,4-dihydropyridine-3,5-dicarboxamide 
• 936820-83-6 2,6-dimethyl-N,N'-bis-(4-nitrophenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxamide 
• 1590368-29-8 5-methyl-N-(4-nitrophenyl)-1-[2-(phenylselanyl)phenyl]-1H-1,2,3-triazole-4-carboxamide 
• 1608483-66-4 8-bromo-4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 1608483-70-0 8-chloro-4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 1608483-63-1 4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 

Relevant articles and documents

Synthesis and biological evaluation of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives

Two new series of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives were synthesized. All the synthesized compounds were evaluated for their antimicrobial activity against Gram-positive bacteria: Staphylococcus aureus MTCC 3160, Bacillus subtilis MTCC 441, Gram-negative bacterium: Escherichia coli MTCC 443 and antifungal activity against Candida albicans MTCC 227 and Aspergillus Niger MTCC 281 and free radical scavenging activity. Compound 7e was found the most active antimicrobial comparable to standards taken. Compounds 7a, 7c, 9a, and 9d also showed significant antibacterial and antifungal activity. Further, compounds 7f, 9d, and 9h showed significant antioxidant activity with IC50 comparable with the standard compound. The synthesized compounds were confirmed for their structure by means of various spectrometric techniques like IR, 1H NMR, mass, and elemental analysis.

Effective microwave synthesis of bioactive thieno[2,3-d]pyrimidines

A series of novel 2-Amino-3-cyanothiophenes (2a-2j) were synthesized using heterogeneous base (K2CO3) supported Gewald reaction. Cyclization of 2a-j with formamide and urea in conventional heating as well as microwave irradiation gave thieno[2,3-d]pyrimidines (3a-3j) and thieno[2,3-d]pyrimidin-2(1H)-ones(4a-4j) respectively. The reaction rates were faster and yields were higher in the microwave conditions. The structures of the compounds were confirmed with elemental analysis, mass spectral analysis, FTIR, 1H NMR and 13C NMR techniques. All the synthesized compounds were subjected to antimicrobial activity (MIC) in vitro by broth dilution method and exhibited a moderate antimicrobial activity.

Design, Multicomponent Synthesis and Characterization of Diversely Substituted Pyrazolo[1,5-a] Pyrimidine Derivatives

The synthesis of various heterocyclic compounds using acetoacetanilide[AAA], we have demonstrated that acetoactanilide are versatile intermediate for the synthesis of pyrazolopyrimidine derivatives. Thus, to explore further, we sought that the reaction of various acetoactanilide, an appropriate aldehyde and 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide in the presence of base in isopropyl alcohol could be an effective strategy to furnish the novel pyrazolopyrimidine derivatives. Here we describe the novel synthetic methodology for the fused pyrazolopyrimidines.