5-Nitrooxindole

Base Information

• Chemical Name: 5-Nitrooxindole
• CAS No.: 20870-79-5
• Molecular Formula: C8H6N2O3
• Molecular Weight: 178.147
• Hs Code.: 2933790090
• European Community (EC) Number: 628-016-9
• NSC Number: 99066,25199
• DSSTox Substance ID: DTXSID50282253
• Wikidata: Q72495081
• Mol file: 20870-79-5.mol

Synonyms:5-Nitrooxindole;20870-79-5;5-nitroindolin-2-one;5-Nitro-2-oxindole;5-nitro-1,3-dihydro-2H-indol-2-one;5-nitro-1,3-dihydroindol-2-one;2H-Indol-2-one, 1,3-dihydro-5-nitro-;MFCD00456999;5-NITRO-2-INDOLINONE;5-NITRO-2,3-DIHYDRO-1H-INDOL-2-ONE;5-Nitro-1,3-dihydroindole-2-one;5-nitrooxindol;5-Nitroindolinon;5-nitro oxindole;5-nitro-oxindole;NSC99066;5-NITRO-1,3-DIHYDRO-INDOL-2-ONE;5-nitro-3H-indol-2-ol;NCIOpen2_002205;SCHEMBL19954;5-Nitro-2-oxindole, 97%;DTXSID50282253;JQCGHRDKVZPCRO-UHFFFAOYSA-N;NSC25199;STR08878;NSC-25199;NSC-99066;STL367534;AKOS000450563;AB06059;AM85661;CS-W008165;PS-3346;AC-22706;SY026862;FT-0638055;EN300-31275;A814990;AG-667/03559046;A1-00365;Q-102618;Z320949678;7-Hydroxy-4-(4-(trifluoromethyl)phenyl)indole-3-acetonitrile

Chemical Property of 5-Nitrooxindole

Chemical Property:

• Appearance/Colour: yellow crystals
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 233-236 °C
• Refractive Index: 1.632
• Boiling Point: 411.375 °C at 760 mmHg
• PKA: 12.61±0.20(Predicted)
• Flash Point: 202.593 °C
• PSA: 74.92000
• Density: 1.45 g/cm³
• LogP: 1.75060
• Storage Temp.: Keep Cold
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 178.03784206
• Heavy Atom Count: 13
• Complexity: 248

Purity/Quality:

99% ^*data from raw suppliers

5-Nitroindolin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)[N+](=O)[O-])NC1=O
• Uses: Reactant for synthesis of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitorsReactant for preparation of Aurora kinase inhibitorsReactant for synthesis of 3-substituted 2-indolinone RET inhibitorsReactant for synthesis of 4-azachromeno[2,3-b]indol-11(6H)-ones and derivatives as analogs of ellipticineReactant for preparation of [18F]fluorobenzylidene-indolinone as possible tyrosine kinase inhibitor for PET tumor imagingReactant for preparation of 3-substituted indolin-2-ones as neuroprotective and toxic agents

Technology Process of 5-Nitrooxindole

There total 17 articles about 5-Nitrooxindole 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: 98.0%

2-oxoindole (59-48-3) → 5-nitrooxindole (20870-79-5)

Guidance literature:

With sulfuric acid; nitric acid; at -15 ℃; for 0.5h;

Reference yield: 81.0%

5-nitroindole (6146-52-7) → 5-nitrooxindole (20870-79-5)

Guidance literature:

With 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one; In 1,4-dioxane; water; at 140 ℃; for 5h;

DOI:10.1002/ejoc.201701807

Reference yield: 78.0%

4-nitro-aniline (100-01-6,104810-17-5) + chloroacetyl chloride (79-04-9) → 5-nitrooxindole (20870-79-5)

Guidance literature:

With montmorillonite KSF; at 20 ℃; for 1.13333h; Sonication; Neat (no solvent);

DOI:10.1016/j.ultsonch.2011.03.023

upstream raw materials:

2-oxoindole

5-Nitro-3-diazo-1,3-dihydro-2H-indol-2-one

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

ethyl 3-methylaminocrotonate

Downstream raw materials:

2,3-dihydro-5-nitro-2-oxo-N-phenyl-1H-indole-1-carboxamide

5-nitro-2-phenoxycarbonyloxy-indole-1-carboxylic acid phenyl ester

Refernces

• 1、 Yao, Dahong,Ruhan,Jiang, Jin,Huang, Jian,Wang, Jinhui,Han, Weina. "Design, synthesis and biological evaluation of 2-indolinone derivatives as PAK1 inhibitors in MDA-MB-231 cells". . . Retrieved 2020.
• 2、 Babkov, Denis A.,Bezsonova, Elena N.,Dubar, Meriam,Klochkov, Vladlen G.,Lozinskaya, Natalia A.,Melekhina, Daria D.,Spasov, Alexander A.,Temnov, Victor V.,Zaryanova, Ekaterina V.. "Towards multi-target antidiabetic agents: In vitro and in vivo evaluation of 3,5-disubstituted indolin-2-one derivatives as novel α-glucosidase inhibitors". supporting information. . Retrieved 2021/11/22.
• 3、 Gao, Min,Gong, Xiangnan,Hu, Lin,Luo, Yanshu,Xia, Yuanzhi,Xu, Qianlan,Zhao, Yukun. "A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles". supporting information. p. 19813 - 19820. Retrieved 2021/08/03.