5-Chloroisatin

Base Information

• Chemical Name: 5-Chloroisatin
• CAS No.: 17630-76-1
• Molecular Formula: C8H4ClNO2
• Molecular Weight: 181.578
• Hs Code.: 29339900
• European Community (EC) Number: 241-614-0
• NSC Number: 135811
• DSSTox Substance ID: DTXSID00170111
• Nikkaji Number: J287.098C
• Wikidata: Q27453018
• ChEMBL ID: CHEMBL327012
• Mol file: 17630-76-1.mol

Synonyms:5-Chlorisatin;5-Chlorisatide;5-chloroindoline-2,3-dione;1H-Indole-2,3-dione, 5-chloro- (9CI);1H-Indole-2,3-dione, 5-chloro-;5-chloro-1H-indole-2,3-dione;

Chemical Property of 5-Chloroisatin

Chemical Property:

• Appearance/Colour: pale yellow to reddish or yellow-brownish powder
• Melting Point: 254-258 °C(lit.)
• Refractive Index: 1.626
• PKA: 8.65±0.20(Predicted)
• PSA: 46.17000
• Density: 1.519g/cm3
• LogP: 1.61280
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: insoluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 180.9930561
• Heavy Atom Count: 12
• Complexity: 241

Purity/Quality:

98% ^*data from raw suppliers

5-Chloroisatin ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)C(=O)C(=O)N2
• Uses: 5-Chloroisatin is a reagent used in the synthesis of Schiff bases through the reaction with 2-methyl-4-nitroaniline or 4-amino-4,5-dihydro-1H-1,2,3-triazole-5-one.

Technology Process of 5-Chloroisatin

There total 46 articles about 5-Chloroisatin 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%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 5-chloroindole 2,3-dione (17630-76-1)

Guidance literature:

With trichloroisocyanuric acid; sulfuric acid; for 0.25h; cooling;

DOI:10.1080/00304940509354956

Reference yield: 96.0%

5-chloro-indolin-2-one (17630-75-0) → 5-chloroindole 2,3-dione (17630-76-1)

Guidance literature:

With oxygen; copper(II) acetate monohydrate; potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 0.5h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2015.02.019

Reference yield: 94.4%

N-tert-butyl-(2-amino-5-chloro-phenyl)-glyoxylamide → 5-chloroindole 2,3-dione (17630-76-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 5h;

upstream raw materials:

N-chloro-succinimide

indole-2,3-dione

5-chloro-2-methoxy-indol-3-one

ethanol

Downstream raw materials:

6-chloro-2-(3-fluoro-4-methoxy-phenyl)-3-methyl-quinoline-4-carboxylic acid

6-chloro-2-(2-fluoro-5-methyl-phenyl)-quinoline-4-carboxylic acid

6-chloro-2-(2-fluoro-5-methyl-phenyl)-3-phenyl-quinoline-4-carboxylic acid

6-chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acid

Refernces

• 1、 De Souza, Soraia P.L.,Da Silva, Joaquim Fernando M.,De Mattos, Marcio C.S.. "Sio2 mediated reaction of isatin with N-halosaccharins: A regiospecific preparation of 5-haloisatins". . p. 31 - 34. Retrieved 2003.
• 2、 Santos, Iara S.,Guerra, Fabiana S.,Bernardino, Lucas F.,Fernandes, Patrícia D.,Hamerski, Lidilhone,Silva, Bárbara V.. "A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity". . p. 198 - 209. Retrieved 2019.
• 3、 Hou, Baolong,Li, Wenyu,Liu, Jianli,Wang, Cuiling,Zhou, Ying. "Synthesis and evaluation of tryptanthrins as antitumor agents". supporting information. . Retrieved 2021/10/01.
• 4、 Patel, Dushyant V.,Patel, Nirav R.,Kanhed, Ashish M.,Teli, Divya M.,Patel, Kishan B.,Gandhi, Pallav M.,Patel, Sagar P.,Chaudhary, Bharat N.,Shah, Dharti B.,Prajapati, Navnit K.,Patel, Kirti V.,Yadav, Mange Ram. "Further Studies on Triazinoindoles as Potential Novel Multitarget-Directed Anti-Alzheimer's Agents". . p. 3557 - 3574. Retrieved 2020/11/18.