158905-35-2

Basic information

• Product Name: 6-chloro-3-Methyl-1h-indole
• Synonyms: 6-chloro-3-Methyl-1h-indole;1H-INDOLE, 6-CHLORO-3-METHYL-;6-chloro-3-methylindole
• CAS NO: 158905-35-2
• Molecular Formula: C₉H₈ClN
• Molecular Weight: 165.61952
• Mol File: 158905-35-2.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-chloro-3-Methyl-1h-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-3-Methyl-1h-indole(158905-35-2)
• EPA Substance Registry System: 6-chloro-3-Methyl-1h-indole(158905-35-2)

Safety Data

• Hazardous Substances Data: 158905-35-2(Hazardous Substances Data)

Usage

Source

Derived from 3-methylindole, a naturally occurring compound in jasmine and other plants

Use

Intermediate in the synthesis of pharmaceuticals and agrochemicals, particularly indole-based drugs and insecticides

Other applications

Potential use in organic synthesis and material science due to unique structure and reactivity

Physical state

Pale yellow solid

Melting point

Approximately 58-60 °C

Synthetic routes

Can be obtained through various synthetic methods

Upstream product

• 441801-03-2 6-chloro-3-methylindole-2-carboxylate 
• 441801-02-1 ethyl 6-chloro-3-methyl-1H-indole-2-carboxylate 
• 148836-41-3 1-bromo-4-chloro-2-iodo-benzene 
• 107-11-9 1-amino-2-propene 
• 133145-48-9 2-(2,4-dichlorophenyl)-2-methyloxirane 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 703-82-2 6-chloro-1H-indole-3-carbaldehyde 
• 17422-33-2 6-chloroindole 
• 67-56-1 methanol 

Downstream Products

• 1028302-45-5 N-trityl-6-chloro-L-tryptophan 
• 769973-17-3 N-trityl-6-chloro-L-tryptophan tert-butyl ester 
• 33468-35-8 6-chloro-DL-tryptophan 
• 1428236-54-7 C₂₀H₁₈ClNO₃ 
• 1640122-69-5 N-acetyl-3-(4-methoxyphenyl)-3-methyl-6-chloroindoline 
• 1640122-87-7 3-(N-acetyl-6-chloro-3-methylindolin-3-yl)-1-tosylindole 

Relevant articles and documents

Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol

A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.

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.

Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).