17422-32-1

Basic information

• Product Name: 5-Chloroindole
• Synonyms: 5-CHLOROINDOLE(5ClI);5-Chloroindole ,98%;5-chloro-1H-indole(SALTDATA: FREE);5-Chloro-1H-indole 98%;5-CHLORO-1H-INDOLE;5-CHLOROINDOLE;1H-Indole,5-chloro-;6-Chloroindole99%
• CAS NO: 17422-32-1
• Molecular Formula: C₈H₆ClN
• Molecular Weight: 151.59
• EINECS: 241-448-9
• Product Categories: Simple Indoles;Pyrroles & Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;IndolesBuilding Blocks;Building Blocks;C7 to C10;C7 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;API Intermediate;NULL;Heterocycle-Indole series;INDOLE;blocks;IndolesOxindoles;Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;IndoleDerivative;Halides;Pyrroles & Indoles;Indoles
• Mol File: 17422-32-1.mol
• Article Data: 50

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 130 °C / 0.4mmHg
• Flash Point: 158.9 °C
• Appearance: White to slightly grayish-green/Crystalline Powder
• Density: 1.1976 (rough estimate)
• Vapor Pressure: 0.00309mmHg at 25°C
• Refractive Index: 1.5437 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in alcohol.
• PKA: 16.09±0.30(Predicted)
• BRN: 2651
• CAS DataBase Reference: 5-Chloroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloroindole(17422-32-1)
• EPA Substance Registry System: 5-Chloroindole(17422-32-1)

Safety Data

• Hazard Codes: Xn,Xi
• 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
• Hazardous Substances Data: 17422-32-1(Hazardous Substances Data)

Usage

Chemical Properties

White to slightly greyish-green crystalline powder

Uses

Different sources of media describe the Uses of 17422-32-1 differently. You can refer to the following data:
1. 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.
2. 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.5570290644The 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.]

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

Upstream product

• 60515-59-5 1-isocyano-4-chloro-2-methylbenzene 
• 32617-55-3 5-chloro-1-p-toluenesulfonylindole 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 873-38-1 4-chloro-2-bromoaniline 
• 10517-21-2 5-chloro-1H-Indole-2-carboxylic acid 
• 771-50-6 1H-indole-3-carboxylic acid 
• 10406-05-0 5-chloro-1H-indole-3-carboxylic acid 
• 10241-98-2 5-Chloro-2,3-dihydro-1H-indole-2-carboxylic acid 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 112768-02-2 4-chloro-1-nitro-2-vinylbenzene 
• 100-00-5 4-chlorobenzonitrile 
• 72301-65-6 α-(5-Chloro-2-nitrophenyl)acetonitrile 
• 1073-69-4 N-4-chlorophenylhydrazine 

Downstream Products

• 15861-24-2 1H-indole-5-carbonitrile 
• 227803-35-2 5-chloro-3-(phenylthio)-1H-indole 
• 54904-22-2 3-(5-chloro-3-1H-indolyl)propanoic acid 
• 92433-38-0 1-benzyl-5-chloro-1H-indole 
• 163160-58-5 (5-chloro-1H-indol-3-yl)-oxo-acetic acid ethyl ester 
• 17630-75-0 5-chloro-indolin-2-one 
• 113423-48-6 3,3-Dibromo-5-chloroindol-2(3H)-one 
• 213542-01-9 5-chloro-3-nitro-1H-indole 
• 85092-85-9 3-iodo-5-chloro-1H-indole 
• 85092-82-6 3-bromo-5-chloro-1H-indole 
• 25658-80-4 5-chloro-2,3-dihydroindole 
• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 78329-47-2 5-chloro-1-(phenylsulfonyl)-1H-indole 
• 92083-31-3 3-(5-Chloro-indol-1-yl)-benzonitrile 

Relevant articles and documents

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring

Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).