5-Nitroisatin

Base Information

• Chemical Name: 5-Nitroisatin
• CAS No.: 611-09-6
• Molecular Formula: C8H4N2O4
• Molecular Weight: 192.131
• Hs Code.: 29337900
• European Community (EC) Number: 210-252-5
• UNII: J4J633881Z
• ChEMBL ID: CHEMBL118305
• DSSTox Substance ID: DTXSID8049331
• Metabolomics Workbench ID: 144386
• Nikkaji Number: J2.990D
• NSC Number: 525798
• Pharos Ligand ID: QJ6BY1KAX581
• Wikidata: Q27281191
• Mol file: 611-09-6.mol

Synonyms:5-Nitroisatin;611-09-6;5-Nitroindoline-2,3-dione;5-Nitro-1H-indole-2,3-dione;5-Nitroindole-2,3-dione;1H-Indole-2,3-dione, 5-nitro-;N-Nitroisatin;Isatin, 5-nitro-;INDOLE-2,3-DIONE, 5-NITRO-;2,3-Dihydro-5-nitroindole-2,3-dione;MFCD00005720;5-Nitro-2,3-indolinedione;CHEMBL118305;DTXSID8049331;J4J633881Z;NSC-525798;5-nitro-2,3-dihydro-1H-indole-2,3-dione;CCRIS 4031;EINECS 210-252-5;NSC 525798;BRN 0180223;5-nitroisatine;5-Nitrosotin;UNII-J4J633881Z;NSC525798;5-Nitroisatin, 97%;Indole-2, 5-nitro-;NITROISATIN, 5-;Isatin-based compound, 37;1H-Indole-2, 5-nitro-;5-21-10-00267 (Beilstein Handbook Reference);SCHEMBL455170;DTXCID3029287;BDBM10299;BDBM22817;UNMYHYODJHKLOC-UHFFFAOYSA-;CHEBI:149791;Tox21_202937;AKOS000200257;AC-5034;CCG-207875;CS-W007582;NCGC00260483-01;5-nitroindoline-2,3-dione;AS-15628;CAS-611-09-6;PD119678;SY039358;FT-0620711;N0572;NS00034572;EN300-17341;O11481;A833047;W-105194;Q27281191;Z56922091;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)

Chemical Property of 5-Nitroisatin

Chemical Property:

• Appearance/Colour: orange-yellow to orange crystalline powder
• Melting Point: 251 °C (dec.)(lit.)
• Refractive Index: 1.657
• Boiling Point: 328.09°C (rough estimate)
• PKA: 8.06±0.20(Predicted)
• PSA: 91.99000
• Density: 1.609 g/cm³
• LogP: 1.39080
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 192.01710661
• Heavy Atom Count: 14
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

5-Nitroisatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40-68-22
• Safety Statements: 7-22-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=O)C(=O)N2
• 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

Technology Process of 5-Nitroisatin

There total 21 articles about 5-Nitroisatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 5-nitroisatin (611-09-6)

Guidance literature:

With sulfuric acid; potassium nitrate; at 20 ℃; for 2h; Cooling with ice;

DOI:10.1007/s11030-018-09910-7

Reference yield: 95.1%

N-tert-butyl-(2-amino-5-nitro-phenyl)-glyoxylamide → 5-nitroisatin (611-09-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 4h;

Reference yield: 91.0%

5-nitrooxindole (20870-79-5) → 5-nitroisatin (611-09-6) + C16H8N4O6

Guidance literature:

With oxygen; sodium iodide; In tetrahydrofuran; at 60 ℃; for 12h; chemoselective reaction; Schlenk technique;

DOI:10.1039/c8cc04471f

upstream raw materials:

3,3-dibromo-5-nitro-indolin-2-one

indole-2,3-dione

hydroxyimino-acetic acid-(4-nitro-anilide)

chloral hydrate

Downstream raw materials:

2-Oxy-6-nitro-chinolin-4-carbonsaeure

2-(4-methyl-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid

2-(4-acetylamino-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid

6-amino-2-phenyl-quinoline-4-carboxylic acid

Refernces

• 1、 Zhuo, Huijun,Zhang, Zhen,Liu, Yang,Zhang, Jingya,Zhao, Guisen. "Design, synthesis and biological evaluation of novel 1,5-disubstituted isatin derivatives as antitumor agents". . p. 2170 - 2180. Retrieved 2020.
• 2、 Jaiswal, Shivani,Ayyannan, Senthil Raja. "Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase". . . Retrieved 2021/11/09.
• 3、 -. "Novel isatin derivative nitration method". Paragraph 0023-0027. . Retrieved 2021/03/31.