5-Chloroisatin - ≥98% , CAS No.17630-76-1

CAS: 17630-76-1 Cat. No.: C134325 Molecular Weight: 181.58 EC Number: 241-614-0

GRADE & PURITY ≥98%

Synonyms

4-methoxy-3-trifluoromethylphenylamine | PD182524 | EN300-17212 | FS-1030 | 1H-Indole-2,3-dione, 5-chloro- | 5-chloroindoline-2,3-dione | 5-amino-4-bromo-1-methylpyrazole | 5-chlor-2,3-dioxoindolin | NSC 135811 | 5-Chloro-1H-indole-2,3-dione | C-5120 | 2H

Storage

Room temperature

Shipped In

Normal

Overview

Product Application:

It was used in synthesis of Schiff base by reaction with 2-methyl-4-nitroaniline.

Product Description:

5-Chloroisatin reacts with substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones to yield Schiff bases.

Specifications

Synonyms

4-methoxy-3-trifluoromethylphenylamine | PD182524 | EN300-17212 | FS-1030 | 1H-Indole-2, 3-dione, 5-chloro- | 5-chloroindoline-2, 3-dione | 5-amino-4-bromo-1-methylpyrazole | 5-chlor-2, 3-dioxoindolin | NSC 135811 | 5-Chloro-1H-indole-2, 3-dione | C-5120 | 2H

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488186405
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186405
• Canonical Smiles: C1=CC2=C(C=C1Cl)C(=O)C(=O)N2
• IUPAC Name: 5-chloro-1H-indole-2,3-dione
• InChIKey: XHDJYQWGFIBCEP-UHFFFAOYSA-N
• INCHI: 1S/C8H4ClNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
• Isomeric SMILES: C1=CC2=C(C=C1Cl)C(=O)C(=O)N2
• WGK Germany: 3
• Molecular Weight: 181.58
• Reaxy-Rn: 383759
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=383759&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolines
• Alternative Parents: Aryl ketones Benzenoids Aryl chlorides Vinylogous amides Secondary carboxylic acid amides Lactams Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Dihydroindole - Aryl ketone - Aryl chloride - Aryl halide - Benzenoid - Vinylogous amide - Carboxamide group - Ketone - Lactam - Secondary carboxylic acid amide - Carboxylic acid derivative - Azacycle - Organochloride - Organohalogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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BCHE Tclin Butyrylcholinesterase (7174 Activities)

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CES1 Tchem Acyl coenzyme A:cholesterol acyltransferase (1029 Activities)

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TGM2 Tchem Protein-glutamine gamma-glutamyltransferase (1221 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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PC-3 (62116 Activities)

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HepG2 (196354 Activities)

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NCI-H460 (60772 Activities)

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Jurkat (10389 Activities)

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SW-620 (52400 Activities)

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ASPC1 (1310 Activities)

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DAO Tchem D-amino-acid oxidase (802 Activities)

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Associated Targets(non-human)

Cruzipain (33337 Activities)

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ALS Acetolactate synthase (354 Activities)

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rhodesain Rhodesain (1463 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Falcipain 2 (539 Activities)

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Brassica rapa subsp. oleifera (1696 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: soluble in water.
• Melt Point(°C): 254-258°C
• Molecular Weight: 181.570 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 180.993 Da
• Monoisotopic Mass: 180.993 Da
• Topological Polar Surface Area: 46.200 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 241.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Cuiling Wang, Jiaxu Yan, Mo Du, Joseph A. Burlison, Chi Li, Yanni Sun, Danqing Zhao, Jianli Liu.  (2017)  One step synthesis of indirubins by reductive coupling of isatins with KBH4.  TETRAHEDRON,      [PMID:] [10.1016/j.tet.2017.03.077]

2. Lin Chen, Han Huang, Xiali Liu, Peijing Zhao, Biao Zhou.  (2025)  Isolation and characterization of a novel oxyphenisatin analogue, 4-Chloro-oxyphenisatin diisobutyrate, from a jelly candy purported to possess weight-loss properties.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:40058082] [10.1016/j.jpba.2025.116804]

3. Shiyao Liu, Hongmin Yu, Zhenhua Liu, Yueyue Zhang, Yutong Han, Yixuan Gu, Yuxuan Li, Zongtao Li, Zhao Wang, Hao Sun.  (2025)  Conjugation-driven electronic structure engineering of halogenated indolequinones for bidirectional catalysis in lithium-sulfur batteries.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.167521]