| Identification | More | [Name]
5-Chloroindole | [CAS]
17422-32-1 | [Synonyms]
5-CHLORO-1H-INDOLE
5-CHLOROINDOLE
1H-Indole,5-chloro-
6-Chloroindole99%
ChloroIndole
5-Chloroindole 98%
1H-Indole,5-chloro-(9CI)
5-CHLOROINDOLE99%
5-chloroindole 17422-32-1 | [EINECS(EC#)]
241-448-9 | [Molecular Formula]
C8H6ClN | [MDL Number]
MFCD00005672 | [Molecular Weight]
151.59 | [MOL File]
17422-32-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to slightly greyish-green crystalline powder | [Melting point ]
69-71 °C (lit.) | [Boiling point ]
130 °C / 0.4mmHg | [density ]
1.1976 (rough estimate) | [refractive index ]
1.5437 (estimate) | [storage temp. ]
2-8°C
| [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
2811 | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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. | [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.] |
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