Description

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).

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.

To prepare the anticancer indoles, a series of substituted heteroannulated indole derivatives has been synthesized and characterized by spectral and elemental analysis. Subsequently they were evaluated for anticancer activity against cervical cancer (HeLa) cell line using MTT assay. Compounds 5c and 5d exhibit excellent activity with the IC50 value of 13.41 and 14.67 µM, respectively which is nearer to the standard cisplatin (IC50-13.20 µM). All the compounds were further screened for their antibacterial activity against five gram negative and two gram positive bacterial strains to assess their selectivity. In order to get more insight into the binding mode and inhibitor binding affinity, compounds (4a–5d) were docked with Human protein kinase CK2. Results suggested that the hydrophobic interactions in the binding pockets of human protein kinase CK2 exploited affinity of the most favorable binding ligands (4c and 5c: glide score = −7.011 and −6.974: E-model score = −50.6 and −50.865, respectively). The structure–activity relationship (SAR) studies demonstrated that the most potent compounds (5c, 5d) can be developed into precise the capability to treat cervical cancer.

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5-Chloroindole (17422-32-1) Specifications

CAS	17422-32-1
CAS Min %	98.0
CAS Max %	100.0
MDL Number	MFCD00005672
InChI Key	ZKAOVABYLXQUTI-UHFFFAOYSA-N
Chemical Name or Material	5-Chloroindole;5-Chloro-1H-indole; 1H-Indole, 5-chloro-; 5-Chloro indole;
Infrared Spectrum	Authentic
Assay Percent Range	98-100%
Physical Form	Crystalline powder
Packaging	Glass bottle
Molecular Formula	C8H6ClN
Molecular Weight (g/mol)	151.593 g/mol
SMILES	C1=CC2=C(C=CN2)C=C1Cl
Color	White to slightly off-white
Chemical Name or Material	5-Chloroindole
Melting Point	69.0-73.0°C
Assay	98%

 

5-Chloroindole (17422-32-1) Safety and Handling

Hazard description (17422-32-1):

Causes skin irritation.

Causes serious eye irritation.

May cause respiratory irritation.

Precautionary statement:

Avoid breathing dust/fume/gas/mist/vapors/spray.

Wear protective gloves/protective clothing/eye protection/face protection.

IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing.

Store locked up.

Dispose of contents/container in accordance with local/regional/national/international regulations.

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

5-Chloroindole (17422-32-1) Articles

5-Chloroindole: a potent allosteric modulator of the 5-HT₃ receptor.

Amy S Newman et. al

British journal of pharmacology (2013-4-19)

Indole and 5-chloroindole as inhibitors of anodic dissolution and cathodic deposition of copper in acidic chloride solutions.

Scendo M, et al. J. Appl.

Electrochem.  (2003)

5-Amino-and 5-chloro-indole as mild steel corrosion inhibitors in 1 N sulphuric acid.

Moretti G, et al.

Electrochimica Acta(1996)

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