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

• 10517-21-2 5-chloro-1H-Indole-2-carboxylic acid 
• 10406-05-0 5-chloro-1H-indole-3-carboxylic acid 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 873-38-1 4-chloro-2-bromoaniline 
• 32617-55-3 5-chloro-1-p-toluenesulfonylindole 
• 60515-59-5 1-isocyano-4-chloro-2-methylbenzene 
• 105896-39-7 N-(4-chlorophenyl)ethenesulfinamide 
• 1826-67-1 vinyl magnesium bromide 
• 100-00-5 4-chlorobenzonitrile 
• 102-71-6 triethanolamine 
• 106-47-8 4-chloro-aniline 
• 180624-15-1 4-chloro-2-trimethylsilanylethynyl-phenylamine 
• 637-39-8 triethanolamine hydrochloride 
• 412947-46-7 4-chloro-2-ethynylaniline 

Downstream Products

• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 75259-79-9 5-chloro-3-<2-(4-pyridyl)ethyl>indole 
• 883-55-6 2-(5-chloro-1H-indol-3-yl)-2-oxoacetyl chloride 
• 92083-31-3 3-(5-Chloro-indol-1-yl)-benzonitrile 
• 78329-47-2 5-chloro-1-(phenylsulfonyl)-1H-indole 
• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 25658-80-4 5-chloro-2,3-dihydroindole 
• 85092-82-6 3-bromo-5-chloro-1H-indole 
• 85092-85-9 3-iodo-5-chloro-1H-indole 
• 213542-01-9 5-chloro-3-nitro-1H-indole 
• 113423-48-6 3,3-Dibromo-5-chloroindol-2(3H)-one 
• 17630-75-0 5-chloro-indolin-2-one 
• 163160-58-5 (5-chloro-1H-indol-3-yl)-oxo-acetic acid ethyl ester 
• 3764-94-1 5-chlorotryptamine 

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.

A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides

A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

Electrosynthesis of Dihydropyrano[4,3-b]indoles Based on a Double Oxidative [3+3] Cycloaddition

Oxidative [3+3] cycloadditions offer an efficient route for six-membered-ring formation. This approach has been realized based on an electrochemical oxidative coupling of indoles/enamines with active methylene compounds followed by tandem 6π-electrocyclization leading to the synthesis of dihydropyrano[4,3-b]indoles and 2,3-dihydrofurans. The radical–radical cross-coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.