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C47604 Sigma-Aldrich

5-Chloroindole

98%

  • CAS Number 17422-32-1

  • Empirical Formula (Hill Notation) C8H6ClN

  • Molecular Weight 151.59

  •  Beilstein/REAXYS Number 2651

  •  EC Number 241-448-9

  •  MDL number MFCD00005672

  •  PubChem Substance ID 24892721

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Halogenated Heterocycles, Heterocyclic Building Blocks,
Quality Level   100
assay   98%
mp   69-71 °C (lit.)
SMILES string   Clc1ccc2[nH]ccc2c1
InChI   1S/C8H6ClN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H
InChI key   MYTGFBZJLDLWQG-UHFFFAOYSA-N

Description

General description

5-Chloroindole can be synthesized by using 3-chlorobenzaldehyde as starting reagent.

5-Chloroindole is a 5-substituted indole. It undergoes electropolymerization to form a redox-active film consisting of a cyclic trimer and chains of linked cyclic trimer (polymer). It is a potential positive allosteric modulator (PAM) of the 5-HT3 receptor. It has been reported as strong inhibitor of the copper dissolution in acidic sodium chloride solution. It has been tested as corrosion inhibitor of mild steel in 1N deaerated sulphuric acid. Synthesis of 5-chloroindole, via nitration of indoline has been described.

Application

5-Chloroindole has been used in the synthesis of 5-chloro-3-indole-N,N- dimethylglyoxalamide and 5-chloro-N,N-dimethyltryptamine. It may be used in the synthesis of dyestuffs in the presence of biocatalysts (Escherichia coli expressing multicomponent phenol hydroxylase (mPH) isolated from Pseudomonas sp. strains KL33 and KL28).

5-Chloroindole has been used to study the biotransformation of substituted indoles to indican derivatives in the tissue cultures of Polygonum tinctorium. It may be employed as a monomer in the preparation of redox-active film made up of a cyclic trimer and chains of linked cyclic trimer (polymer).

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Indoles

Sigma-Aldrich is proud to offer a new series of ChemFiles—called Privileged Structures, to our Drug Discovery and Organic Synthesis customers. Each piece will highlight a specific motif, selected app...
Chemfiles Volume 4 Article 8
Keywords: Building blocks, Cardiovascular, Diabetes, Diseases, Drug discovery, Medicinal chemistry, Organic synthesis, Respiratory

Peer-Reviewed Papers
15

References

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