1-(2,6-Dichlorophenyl)-2-indolinone

Base Information

• Chemical Name: 1-(2,6-Dichlorophenyl)-2-indolinone
• CAS No.: 15362-40-0
• Molecular Formula: C14H9Cl2NO
• Molecular Weight: 278.138
• Hs Code.: 29337900
• European Community (EC) Number: 239-399-3,928-201-7
• NSC Number: 621845
• UNII: CL5Y02756K
• DSSTox Substance ID: DTXSID6046979
• Nikkaji Number: J26.825I
• Wikidata: Q27275517
• ChEMBL ID: CHEMBL487716
• Mol file: 15362-40-0.mol

Synonyms:1-(2,6-dichlorophenyl)indolin-2-one;1-(DCP)I

Chemical Property of 1-(2,6-Dichlorophenyl)-2-indolinone

Chemical Property:

• Melting Point: 115-119°C
• Boiling Point: 488.6 ºC at 760 mmHg
• PKA: -4.85±0.20(Predicted)
• Flash Point: 249.3 ºC
• PSA: 20.31000
• Density: 1.432 g/cm³
• LogP: 4.27920
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 277.0061193
• Heavy Atom Count: 18
• Complexity: 326

Purity/Quality:

99% ^*data from raw suppliers

DiclofenacAmide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2N(C1=O)C3=C(C=CC=C3Cl)Cl
• Uses: 1-(2,6-Dichlorophenyl)indolin-2-one is a potential prodrug of Diclofenac and possible impurity during its commercial synthesis. It is Aceclofenac EP Impurity I and Diclofenac Impurity A.

Technology Process of 1-(2,6-Dichlorophenyl)-2-indolinone

There total 41 articles about 1-(2,6-Dichlorophenyl)-2-indolinone 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: 97.0%

1-(2,6-dichlorophenyl)-3-(methylthio)oxindole (83281-94-1) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Guidance literature:

With zinc; In acetic acid; for 4h; Heating;

DOI:10.1248/cpb.32.1995

Reference yield: 94.0%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.3390/molecules14093187

Reference yield: 93.0%

2,2-dimethyl-1,3-dioxolane (2916-31-6) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 5-(2,6-dichloro-phenyl)-6,6-dimethyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Guidance literature:

With toluene-4-sulfonic acid; In ethanol;

upstream raw materials:

2-chloro-N-(2,6-dichlorophenyl)acetamide

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide

1-(2,6-dichlorophenyl)-3-(methylthio)oxindole

2,2-dimethyl-1,3-dioxolane

Downstream raw materials:

diclofenac sodium

1-(2,6-Dichlorophenyl)-3-(dimethylaminomethylene)-6-formylindolin-2-one

1-(2',6'-dichlorophenyl)-3-dimethylaminomethylene-2-indolinone

1-(2,6-Dichlorophenyl)-3-hydroxymethylene-6-formylindolin-2-one

Refernces

• 1、 Chung, Man Chin,Dos Santos, Jean Leandro,Oliveira, Ednir Vizioli,Blau, Lorena,Renato Farina Menegon,Peccinini, Rosangela Goncalves. "Synthesis, ex vivo and in vitro hydrolysis study of an indoline derivative designed as an anti-inflammatory with reduced gastric ulceration properties". . p. 3187 - 3197. Retrieved 2009.
• 2、 Roy, Jiben,Islam, Mafizul,Khan, Anowar H.,Das, Subodh C.,Akhteruzzaman,Deb, Ajay K.,Mahbub Alam. "Diclofenac sodium injection sterilized by autoclave and the occurrence of cyclic reaction producing a small amount of impurity". . p. 541 - 544. Retrieved 2001.
• 3、 Galisteo, Alberto,Jannus, Fatin,García-García, Amalia,Aheget, Houssam,Rojas, Sara,Lupia?ez, José A.,Rodríguez-Diéguez, Antonio,Reyes-Zurita, Fernando J.,Quílez Del Moral, José F.. "Diclofenac n-derivatives as therapeutic agents with anti-inflammatory and anti-cancer effect". . . Retrieved 2021/05/18.
• 4、 Fu, Yongsheng,Liu, Yiqing,Zhang, Li. "Degradation kinetics and mechanism of diclofenac by UV/peracetic acid". . p. 9907 - 9916. Retrieved 2020/03/23.