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HomeProduct name list5-Chloroindole

5-Chloroindole

  • CAS NO.:17422-32-1
  • Empirical Formula: C8H6ClN
  • Molecular Weight: 151.59
  • MDL number: MFCD00005672
  • EINECS: 241-448-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-29 11:48:30
5-Chloroindole Structural

What is 5-Chloroindole?

Chemical properties

White to slightly greyish-green crystalline powder

The Uses of 5-Chloroindole

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.

The Uses of 5-Chloroindole

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

What are the applications of Application

5-Chloroindole is a compund which has been has been shown to depress serotonin levels

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.]

Properties of 5-Chloroindole

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
CAS DataBase Reference 17422-32-1(CAS DataBase Reference)

Safety information for 5-Chloroindole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 5-Chloroindole

InChIKey MYTGFBZJLDLWQG-UHFFFAOYSA-N

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