17422-33-2

Basic information

• Product Name: 6-Chloroindole
• Synonyms: 6-chloroindole 17422-32-2;6-chloro-1H-indole(SALTDATA: FREE);NSC 58083;6-Chloroindole, 97+%;1H-Indole, 6-chloro-;TIMTEC-BB SBB004059;6-CHLORO-1H-INDOLE;6-CHLOROINDOLE
• CAS NO: 17422-33-2
• Molecular Formula: C₈H₆ClN
• Molecular Weight: 151.59
• EINECS: 241-449-4
• Product Categories: Indoles;Simple Indoles;Indole Derivatives;Halogenated Heterocycles;Heterocyclic Building Blocks;IndolesBuilding Blocks;Building Blocks;C7 to C10;C7 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Indole series;INDOLE;blocks;IndolesOxindoles;Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives
• Mol File: 17422-33-2.mol
• Article Data: 35

Chemical Properties

• Melting Point: 87-90 °C(lit.)
• Boiling Point: 248.91°C (rough estimate)
• Flash Point: 158.9 °C
• Appearance: Beige/Crystalline Powder
• Density: 1.1976 (rough estimate)
• Vapor Pressure: 0.00309mmHg at 25°C
• Refractive Index: 1.5437 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: slightly soluble
• PKA: 16.10±0.30(Predicted)
• Water Solubility: slightly soluble
• Stability: Store in Refrigerator
• BRN: 112345
• CAS DataBase Reference: 6-Chloroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloroindole(17422-33-2)
• EPA Substance Registry System: 6-Chloroindole(17422-33-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• TSCA: A
• Hazardous Substances Data: 17422-33-2(Hazardous Substances Data)

Usage

Chemical Properties

Light Orange Powder

Uses

6-Chloroindole (cas# 17422-33-2) is a compound useful in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 580, 1990 DOI: 10.1021/jo00289a036

General Description

6-Chloroindole, when added to Claviceps purpurea, produced the corresponding substituted L-tryptophan.

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

Upstream product

• 75-07-0 acetaldehyde 
• 108-42-9 3-chloro-aniline 
• 31271-88-2 6-chloro-N-p-tolylsulfonylindole 
• 56341-37-8 6-chloro-2-oxindole 
• 89-61-2 2,5-dichloronitrobenzene 
• 65547-99-1 ethyl 2-(4-chloro-2-nitrophenyl)-2-cyanoacetate 
• 87081-90-1 (4-chloro-2-nitro-phenyl)-acetonitrile 
• 27034-51-1 ethyl 6-chloro-1H-indole-2-carboxylate 
• 14763-20-3 3-chlorophenyl hydrazine 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 90001-58-4 4-chloro-2,β-dinitro-styrene 
• 89-59-8 4-chloro-2-nitrotoluene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 32989-56-3 5-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene 

Downstream Products

• 147621-19-0 6-(pyridin-3-yl)-1H-indole 
• 947589-64-2 3-acetyl-1-(2,6-difluorobenzyl)-6-chloro-1H-indole 
• 486446-41-7 N-(3-{1-[(6-chloro-1H-indol-3-yl)methyl]-4-piperidinyl}phenyl)-2-methylpropanamide 
• 1314043-48-5 (R)-1-benzyl-5-(6-chloro-1H-indol-1-yl)pyrrolidin-2-one 
• 1383456-31-2 (R)-3-phenyl-1-(6-chloro-1H-indol-3-yl)-2-tosyl-1,2-dihydroisoquinoline 
• 147621-18-9 6-indolylboronic acid 
• 1423754-12-4 C₁₇H₁₃ClN₂O₄S 
• 1423754-18-0 (S)-2-((R)-1-(6-chloro-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal 
• 388574-11-6 6-Chloro-1-methylindole-3-acetic acid 
• 1912-44-3 6-chloroindole-3-acetic acid 
• 241498-59-9 4-(1-benzhydryl-6-chloro-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid methyl ester 

Relevant articles and documents

Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies

A series of platinum(II) complexes supported by terphenyl diacetylide as well as diimine or bis-N-heterocyclic carbene (NHC) ligands have been prepared. The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties as revealed by X-ray crystallographic analyses. The electrochemical, photophysical and photochemical properties of these platinum(II) complexes have been investigated. These platinum(II) diimine complexes show broad emission with peak maxima from 566 nm to 706 nm, with two of them having emission quantum yields >60% and lifetimes 2 μs in solutions at room temperature, whereas the platinum(II) diacetylide complexes having bis-N-heterocyclic carbene instead of diimine ligand display photoluminescence with quantum yields of up to 28% in solutions and excited state lifetimes of up to 62 μs at room temperature. Application studies revealed that one of the complexes can catalyze photoinduced aerobic dehydrogenation of alcohols and alkenes, and a relatively non-toxic water-soluble Pt(II) complex displays anti-angiogenic activity.

Method for catalytically synthesizing indole derivative by using ferrous complex

The invention relates to a method for catalytically synthesizing an indole derivative by using a ferrous complex, which comprises the following step: by taking arylamine and acetaldehyde as raw materials and a ferrous complex containing a meta-carboboryl methylpyridine structure as a catalyst, conducting reacting at room temperature to prepare the indole derivative. Compared with the prior art, the method utilizes the ferrous complex to efficiently catalyze the reaction of arylamine and acetaldehyde at room temperature to prepare the indole derivative, the reaction condition is mild, the substrate range is wide, and the method has high catalytic activity and yield.

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.).