5-Aminooxindole

Base Information

• Chemical Name: 5-Aminooxindole
• CAS No.: 20876-36-2
• Molecular Formula: C8H8N2O
• Molecular Weight: 148.164
• Hs Code.: 2933790090
• European Community (EC) Number: 633-807-7
• DSSTox Substance ID: DTXSID90378285
• Nikkaji Number: J83.040B
• Wikidata: Q72440231
• Mol file: 20876-36-2.mol

Synonyms:5-Aminooxindole;20876-36-2;5-aminoindolin-2-one;5-Amino-1,3-dihydro-indol-2-one;5-amino-1,3-dihydroindol-2-one;2H-Indol-2-one, 5-amino-1,3-dihydro-;5-Amino-2-indolinone;5-AMINO-2,3-DIHYDRO-1H-INDOL-2-ONE;MFCD02179603;5-Amino-2-oxindole;5-aminooxindol;5-Amino-oxindol;5-amino oxindole;5-amino-oxindole;SCHEMBL22660;DTXSID90378285;5-Amino-1H-indole-2(3H)-one;JPUYXUBUJJDJNL-UHFFFAOYSA-N;AM844;5-amino-1,3-dihydro-indol-2-on;5-amino 1,3-dihydro-indol-2-one;AKOS000158085;CS-W010983;PB27577;PS-3297;5-amino-1,3-dihydro-2H-indol-2-one;AC-23420;SY031781;A4542;BB 0237564;FT-0601090;EN300-59131;VU0240158-3;5-Amino-1,3-dihydro-indol-2-one, AldrichCPR;F2189-0265;2-AMINO-3-(3-BENZYL-3H-IMIDAZOL-4-YL)-PROPIONICACID

Chemical Property of 5-Aminooxindole

Chemical Property:

• Appearance/Colour: Yellow to brown crystalline powder
• Vapor Pressure: 3.73E-07mmHg at 25°C
• Melting Point: 182-186 °C
• Refractive Index: 1.653
• Boiling Point: 416.8 °C at 760 mmHg
• PKA: 13.91±0.20(Predicted)
• Flash Point: 205.8 °C
• PSA: 55.12000
• Density: 1.307 g/cm³
• LogP: 1.48260
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.063662883
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-2-indolinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)N)NC1=O
• Uses: 5-Amino-2-indolinone is useful in the synthesis of anticancer drugs, Cyclin dependent kinase inhibitors and spleen tyrosine kinase (Syk) inhibitors.

Technology Process of 5-Aminooxindole

There total 7 articles about 5-Aminooxindole 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: 100.0%

5-nitrooxindole (20870-79-5) → 5-amino-1,3-dihydro-2H-indol-2-one (20876-36-2)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; at 20 ℃; for 1h; under 760.051 Torr;

Reference yield: 90.0%

2-oxoindole (59-48-3) → 5-amino-1,3-dihydro-2H-indol-2-one (20876-36-2)

Guidance literature:

With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide; In 2,2,2-trifluoroethanol; water; at 30 ℃; for 2h;

DOI:10.1002/chem.201605476

Reference yield: 82.0%

bromide perbromide + 5-nitroindole (6146-52-7) → 5-amino-1,3-dihydro-2H-indol-2-one (20876-36-2)

Guidance literature:

With zinc; In water; acetic acid; ethyl acetate; tert-butyl alcohol;

upstream raw materials:

5-nitrooxindole

2-oxoindole

5-nitroindole

5-Aminoisatin

Downstream raw materials:

5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]oxindol

5-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2,3-dihydro-1H-indol-2-one

N-methyl-2-{[2-[(2-oxo-2,3-dihydro-1H-indol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}benzamide

N-methyl-2-({5-methyl-2-[(2-oxo-2.3-dihydro-1H-indol-5-yl)amino]-4-pyridinyl}amino)benzamide

Refernces

• 1、 Zhang, Chenzi,Kuang, Xinyi,Zhou, Yuanzheng,Peng, Xian,Guo, Qiang,Yang, Tao,Zhou, Xuedong,Luo, Youfu,Xu, Xin. "A novel small molecule, ZY354, inhibits dental caries-associated oral biofilms". . . Retrieved 2019.
• 2、 Romagnoli, Romeo,Baraldi, Pier Giovanni,Prencipe, Filippo,Oliva, Paola,Baraldi, Stefania,Salvador, Maria Kimatrai,Lopez-Cara, Luisa Carlota,Bortolozzi, Roberta,Mattiuzzo, Elena,Basso, Giuseppe,Viola, Giampietro. "Design, synthesis and biological evaluation of 3-substituted-2-oxindole hybrid derivatives as novel anticancer agents". . p. 258 - 270. Retrieved 2017.
• 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.