611-09-6

Basic information

• Product Name: 5-Nitroisatin
• Synonyms: 1H-Indole-2,3-dione,5-nitro-;5-nitro-1h-indole-3-dione;5-nitro-indole-3-dione;5-nitro-isati;Indole-2,3-dione, 5-nitro-;Isatin, 5-nitro-;2,3-dihydro-5-nitroindole-2,3-dione;Nitroisatin
• CAS NO: 611-09-6
• Molecular Formula: C₈H₄N₂O₄
• Molecular Weight: 192.13
• EINECS: 210-252-5
• Product Categories: Indane/Indanone and Derivatives;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 611-09-6.mol
• Article Data: 58

Chemical Properties

• Melting Point: 251 °C (dec.)(lit.)
• Boiling Point: 328.09°C (rough estimate)
• Appearance: Orange-yellow to orange/Crystalline Powder
• Density: 1.5513 (rough estimate)
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.06±0.20(Predicted)
• BRN: 180223
• CAS DataBase Reference: 5-Nitroisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitroisatin(611-09-6)
• EPA Substance Registry System: 5-Nitroisatin(611-09-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40-68-22
• Safety Statements: 7-22-36/37/39-45-36/37
• RIDADR: 2811
• WGK Germany: 3
• RTECS: NL7970000
• HazardClass: IRRITANT
• Hazardous Substances Data: 611-09-6(Hazardous Substances Data)

Usage

Preparation

Isatin 30 (14.7 g, 0.1 mol) was added to conc. H2SO4 (121 ml) ?cooled to 0 oC in an ice-salt bath. Fuming HNO3 (4.2 ml) was ?added to this, drop by drop, in such a way that temperature should ?not rise above 5 oC. The reaction mixture was allowed to stand for ?about 30 minutes and then poured over crushed ice (500 g). A yellow precipitate separated ?immediately. The 5-Nitroisatin was filtered and washed with water and air dried to a constant ?weight (15 g). ?Yield : 85%

Chemical Properties

orange-yellow to orange crystalline powder

Uses

Reactant for preparation of:Potential antibacterial and antifungal agentsspiro[indole-thiazolidinones] as a medicinally important scaffoldPotential antimycobacterial agentsAnticonvulsant agentsInhibitors of human transglutaminase 2Anthelmintic agentsAnti-human immunodeficiency virus (HIV) agentsAntimicrobial agentsPotential antitubercular agentsInhibitors of acetylcholinesterase

InChI:InChI=1/C8H4N2O4/c11-7-5-3-4(10(13)14)1-2-6(5)9-8(7)12/h1-3H,(H,9,11,12)

Upstream product

• 113423-47-5 3,3-dibromo-5-nitro-indolin-2-one 
• 91-56-5 indole-2,3-dione 
• 17122-62-2 hydroxyimino-acetic acid-(4-nitro-anilide) 
• 302-17-0 chloral hydrate 
• 100-01-6 4-nitro-aniline 
• 6146-52-7 5-nitroindole 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 16135-31-2 p-nitroformanilide 
• 79-37-8 oxalyl dichloride 
• 125600-42-2 2-amino-5-nitrophenylacetylene 
• 20870-79-5 5-nitrooxindole 
• 908295-26-1 3-iodo-5-nitro-1H-indole 

Downstream Products

• 55764-56-2 2-Oxy-6-nitro-chinolin-4-carbonsaeure 
• 109068-69-1 2-(4-methyl-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 108237-12-3 2-(4-acetylamino-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 109540-22-9 6-amino-2-phenyl-quinoline-4-carboxylic acid 
• 835901-20-7 2,2'-diphenyl-[6,6']azoxyquinoline-4,4'-dicarboxylic acid 
• 109068-71-5 2-(4-methoxy-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 42816-53-5 5-Aminoisatin 
• 73271-58-6 1-morpholin-4-ylmethyl-5-nitro-3-p-tolylimino-1,3-dihydro-indol-2-one 
• 73271-59-7 3-(2-ethoxy-phenylimino)-1-morpholin-4-ylmethyl-5-nitro-1,3-dihydro-indol-2-one 
• 83393-63-9 3-(2-Furan-2-yl-2-oxo-ethyl)-3-hydroxy-5-nitro-1,3-dihydro-indol-2-one 
• 129222-32-8 7-amino-1,2,3,4-tetrahydro-3-oxoacridine-9-carboxylic acid ethylene ketal 
• 129222-31-7 7-<5-(2-hydroxyethyloxy)-2-hydroxy>phenylamino-1,2,3,4-tetrahydro-3-oxoacridine-9-carboxylic acid ethylene ketal 
• 94493-38-6 4-hydroxy-2,3'-(5-nitro-oxindolydine)-4-phenylbut-3-enoic lactone 
• 77603-42-0 8-nitroindolo[2,1-b]quinazoline-6,12-dione 

Relevant articles and documents

Synthesis, antioxidant activity and SAR study of novel spiro-isatin-based Schiff bases

Abstract: A new series of 21 Schiff bases of spiro-isatin was synthesized, and their DPPH, CUPRAC and ABTS cation radical scavenging abilities were investigated for antioxidant activity. The results showed that all the synthesized compounds exhibited anti

Novel method for synthesis of isatins [3]

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Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives

The synthesis of novel indole derivatives 4a-o using a microwave assisted method via Schiff’s base and Mannich base reaction mechanism was described. Compounds 3a-c were synthesized via reaction of 2-amino benzothiazole with substituted isatin by Schiff base reaction mechanism. Also, indole derivatives 4a-o were synthesized via reaction of compounds 3a-c with substituted benzaldehydes by Mannich base reaction. The biological potentials of the newly synthesized indole derivatives were evaluated for their anthelmintic activity and in vitro anticancer activity by MTT assay. The anticancer activity results suggested that indole derivatives 4c-o have activity against MCF-7 and SKOV3 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of these novel derivatives of indole showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was also investigated.

Isoxazole formamido-4 (3H)-quinazolinone derivative as well as synthesis method and application thereof

The invention relates to a 6-(isoxazolyl-3-formamido)-4 (3H)-quinazolinone derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituent groups. The invention discloses structures and synthesis methods of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activity of protein tyrosine phosphatase, and the compounds can be further developed into drugs for treating Alzheimer's disease.