Merck
CN

C47604

Sigma-Aldrich

5-氯吲哚

98%

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经验公式(希尔记法):
C8H6ClN
CAS号:
分子量:
151.59
Beilstein:
2651
EC 号:
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

检测方案

98%

形式

crystals

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

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一般描述

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.

应用

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).

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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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)
Synthesis of Some 5-and 6-Chloro, 5-Methyl, and 5, 6, 7-Trimethyl Derivatives of Tryptamine.
Benington F, et al.
The Journal of Organic Chemistry, 25(9), 1542-1547 (1960)
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
Fluorescence properties of electropolymerised 5-substituted indoles in solution.
Jennings P, et al.
J. Chem. Soc., Faraday, 94(24), 3619-3624 (1998)

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