5-Chloroindole Chemical Properties

Melting point:

69-71 °C (lit.)

Boiling point:

130 °C / 0.4mmHg

Density 

1.1976 (rough estimate)

refractive index 

1.5437 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in alcohol.

form 

Crystalline Powder

pka

16.09±0.30(Predicted)

color 

White to slightly grayish-green

BRN 

2651

InChIKey

MYTGFBZJLDLWQG-UHFFFAOYSA-N

CAS DataBase Reference

17422-32-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-36-26-37/39

RIDADR 

2811

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29339990

MSDS

• Language:English Provider:5-Chloroindole
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5-Chloroindole Usage And Synthesis

Chemical Properties

White to slightly greyish-green crystalline powder

Uses

5-Chloroindole is a halo-substituted indole used in the preparation of neurologically active compounds such as atypical antipsychotic agents. 5-Chloroindole has been shown to depress serotonin levels in the brainstem and telencephalon.

Uses

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

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 29, p. 1625, 1992 DOI: 10.1002/jhet.5570290644
The Journal of Organic Chemistry, 44, p. 578, 1979 DOI: 10.1021/jo01318a021

General Description

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.

Purification Methods

It is distilled at high vacuum and recrystallises from pet ether (b 40-60o) or (b 80-100o) as glistening plates. The picrate has m 147o (146.5-147.5o)(from *C6H6). [Rydon & Tweddle J Chem Soc 3499 1955, Sugasawa J Org Chem 44 578 1979, Beilstein 20/4 V 34.]

5-Chloroindole(17422-32-1)Related Product Information

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