17422-33-2

Usage

Uses

Used in Organic Synthesis:
6-Chloroindole is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Chloroindole is used as a key component in the development of new drugs. Its ability to form stable bonds with other molecules makes it suitable for the creation of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
6-Chloroindole also finds application in the agrochemical industry, where it is utilized in the synthesis of new pesticides and herbicides. Its chemical properties enable the development of effective and targeted agrochemicals that can help improve crop yields and protect plants from pests and diseases.
Used in Research and Development:
In the field of research and development, 6-Chloroindole serves as a valuable compound for studying the properties and behavior of indole derivatives. It is used in academic and industrial laboratories to explore new chemical reactions and develop innovative synthetic methods.
Used in Chemical Production:
6-Chloroindole is also used in the production of various specialty chemicals, such as dyes, pigments, and other organic compounds. Its versatility and reactivity make it an essential component in the manufacturing process of these products.

Synthesis Reference(s)

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

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

Upstream product

• 16732-75-5 6-chloro-1H-indole-2-carboxylic acid 
• 766557-02-2 6-chloro-1H-indole-3-carboxylic acid 
• 52537-00-5 6-chloroindoline 
• 22630-08-6 tris(piperidino)-methane 
• 89-59-8 4-chloro-2-nitrotoluene 
• 121-73-3 3-Nitrochlorobenzene 
• 1826-67-1 vinyl magnesium bromide 
• 16764-17-3 2-(4-chloro-2-nitrophenyl)ethan-1-ol 
• 69111-49-5 2-nitro-4-chlorophenylacetaldehyde 
• 124043-86-3 2-(2-amino-4-chlorophenyl)ethan-1-ol 
• 88131-68-4 6-Chloro-1-(methylsulfonyl)indole 
• 85355-58-4 1-(2-Bromo-2-chloro-ethyl)-4-chloro-2-nitro-benzene 
• 54664-52-7 4-chloro-β-phenethylsulfonyl azide 
• 85355-38-0 Acetic acid 1-chloro-2-(4-chloro-2-nitro-phenyl)-ethyl ester 

Downstream Products

• 1912-44-3 6-chloroindole-3-acetic acid 
• 180160-77-4 6-Chloro-3-(1,2,3,6-Tetrahydro-4-pyridinyl)-1H-indole 
• 126496-86-4 (R)-2-Benzyloxycarbonylamino-3-(6-chloro-1H-indol-3-yl)-propionic acid benzyl ester 
• 155868-51-2 6-chloro-1-methyl-1H-indole 
• 126759-61-3 1-(6-chloroindol-1-yl)ethanone 
• 3670-19-7 2-(6-chloro-1H-indole-3-yl)ethan-1-amine 
• 120-72-9 indole 
• 1392273-26-5 (6-chloro-1H-indol-3-yl)acetic acid ethyl ester 
• 703-82-2 6-chloro-1H-indole-3-carbaldehyde 
• 596105-56-5 4-(6-chloro-1H-indol-3-yl)butan-2-one 
• 241498-69-1 4-(6-chloro-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid methyl ester 
• 92161-72-3 6-chloro-3-(phenylthio)-1H-indole 
• 868694-20-6 6-chloro-3-iodo-1H-indole 
• 50517-12-9 1-(6-chloro-1H-indol-3-yl)-N,N-dimethylmethanamine 

Relevant academic research and scientific papers

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.

Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis

A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.

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.

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.

Decarboxylation of indole-3-carboxylic acids under metal-free conditions

Two reaction systems have been developed for the decarboxylation of indole-3-carboxylic acids. The decarboxylation can be achieved smoothly under K2CO3-catalyzed or acetonitrile-promoted basic conditions. It provided an efficient and simple method for the transformation of indole-3-carboxylic acids and the corresponding indoles were isolated with good to excellent yields. From the experimental facts, we put forward the possible reaction mechanism.

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.).

Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines

Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed isotopic labeling experiments, control experiments, and kinetic studies provided cumulative evidence to elucidate the reaction mechanism.

Applications of rare earth silicon amination material as catalyst in preparation of indole or indole derivative

The invention belongs to the technical field of chemical engineering, and specially provides applications of a rare earth silicon amination material as a catalyst in preparation of indole or an indolederivative, wherein the reaction raw materials comprise a compound I, the general formula of the compound I is shown in the specification, R is hydrogen, methyl, chlorine, fluorine, bromine or methoxyl, the rare earth silicon amination material M[N(SiMe3)2]3 is a catalyst, and M is a rare earth element. According to the invention, the indole or the indole derivative is prepared by taking the rareearth silicon amination material as the catalyst and taking the compound I and pinacol boron as the raw materials; the method is simple and convenient to operate and high in reaction selectivity; andthe synthesized indole derivative is good in product quality and high in yield.

Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes

Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.

A indole compound and its preparation method and application (by machine translation)

The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)