5-Hydroxyoxindole

Base Information

• Chemical Name: 5-Hydroxyoxindole
• CAS No.: 3416-18-0
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 2933790090
• European Community (EC) Number: 222-309-1
• DSSTox Substance ID: DTXSID20187761
• Nikkaji Number: J182A
• Wikidata: Q72480882
• Metabolomics Workbench ID: 130271
• ChEMBL ID: CHEMBL3093623
• Mol file: 3416-18-0.mol

Synonyms:5-hydroxyoxindole

Chemical Property of 5-Hydroxyoxindole

Chemical Property:

• Vapor Pressure: 1.21E-07mmHg at 25°C
• Melting Point: 156-157 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.634
• Boiling Point: 419.858 °C at 760 mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 207.723 °C
• PSA: 49.33000
• Density: 1.362 g/cm³
• LogP: 1.02480
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)O)NC1=O

Technology Process of 5-Hydroxyoxindole

There total 16 articles about 5-Hydroxyoxindole 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: 81.0%

2-oxoindole (59-48-3) → 5-hydroxyoxindole (3416-18-0)

Guidance literature:

With trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; In chloroform; at 20 ℃; for 25h;

DOI:10.1021/jo0260847

Reference yield: 72.0%

5-Hydroxy-1-methoxy-1,3-dihydro-indol-2-one (121989-51-3) → 5-hydroxyoxindole (3416-18-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00275a027

Reference yield: 65.0%

6-methoxyoxindole (7699-19-6) → 5-hydroxyoxindole (3416-18-0)

Guidance literature:

With water; hydrogen bromide; at 120 ℃; for 16h;

upstream raw materials:

2-Ethoxy-5-hydroxy-3-indolcarbonsaeure-ethylester

N-(4-methoxyphenyl)-2-chloroacetamide

1-methoxyindolin-2-one

5-Hydroxy-1-methoxy-1,3-dihydro-indol-2-one

Downstream raw materials:

C₂₀H₁₉N₅O₄

Refernces

• 1、 Andreani, Aldo,Granaiola, Massimiliano,Leoni, Alberto,Locatelli, Alessandra,Morigi, Rita,Rambaldi, Mirella,Garaliene, Vida. "Synthesis and antitumor activity of 1,5,6-substituted E-3-(2-chloro-3-indolylmethylene)-1,3-dihydroindol-2-ones". . p. 2666 - 2669. Retrieved 2002.
• 2、 Ngai, Mun Hong,So, Choon Leng,Sullivan, Michael B.,Ho, Han Kiat,Chai, Christina L. L.. "Photoinduced Isomerization and Hepatoxicities of Semaxanib, Sunitinib and Related 3-Substituted Indolin-2-ones". . p. 72 - 80. Retrieved 2016/01/15.
• 3、 Xu, Xiu-Hua,Wang, Xin,Liu, Guo-Kai,Tokunaga, Etsuko,Shibata, Norio. "Regioselective synthesis of heteroaryl triflones by LDA (lithium diisopropylamide)-mediated anionic thia-Fries rearrangement". supporting information; experimental part. p. 2544 - 2547. Retrieved 2012/07/14.