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C47604

Sigma-Aldrich

5-Chloroindole

98%

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About This Item

Formule empirique (notation de Hill):
C8H6ClN
Numéro CAS:
17422-32-1
Poids moléculaire :
151.59
Numéro Beilstein :
2651
Numéro CE :
241-448-9
Numéro MDL:
MFCD00005672
Code UNSPSC :
12352100
ID de substance PubChem :
24892721
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

98%

Forme

crystals

Pf

69-71 °C (lit.)

Chaîne SMILES 

Clc1ccc2[nH]ccc2c1

InChI

1S/C8H6ClN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

Clé InChI

MYTGFBZJLDLWQG-UHFFFAOYSA-N

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Description générale

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Xiaoxue Tong et al.
Microbial cell factories, 15(1), 180-180 (2016-10-23)
Engineering of single-species biofilms for enzymatic generation of fine chemicals is attractive. We have recently demonstrated the utility of an engineered Escherichia coli biofilm as a platform for synthesis of 5-halotryptophan. E. coli PHL644, expressing a recombinant tryptophan synthase, was
Fluorescence properties of electropolymerised 5-substituted indoles in solution.
Jennings P, et al.
J. Chem. Soc., Faraday Trans., 94(24), 3619-3624 (1998)
Indigo and indirubin derivatives from indoles in Polygonum tinctorium tissue cultures.
Shim JY, et al.
Biotechnology Letters, 20(12), 1139-1143 (1998)
5-Amino-and 5-chloro-indole as mild steel corrosion inhibitors in 1 N sulphuric acid.
Moretti G, et al.
Electrochimica Acta, 41(13), 1971-1980 (1996)
Amy S Newman et al.
British journal of pharmacology, 169(6), 1228-1238 (2013-04-19)
The 5-HT₃ receptor is a ligand-gated ion channel that is modulated allosterically by various compounds including colchicine, alcohols and volatile anaesthetics. However the positive allosteric modulators (PAMs) identified to date have low affinity, which hinders investigation because of non-selective effects
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