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

• 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 
• 67-56-1 methanol 
• 17422-33-2 6-chloroindole 
• 703-82-2 6-chloro-1H-indole-3-carbaldehyde 
• 441801-02-1 ethyl 6-chloro-3-methyl-1H-indole-2-carboxylate 
• 441801-03-2 6-chloro-3-methylindole-2-carboxylate 

Downstream Products

• 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

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles

A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2- a]indoles via Dynamic Kinetic Resolution of Allene Intermediates

We report the chiral phosphoric acid catalyzed formal (3 + 2) cycloaddition of 3-substituted 1H-indoles and propargylic alcohols containing a functional directing group (p-NHAc or p-OH). This work represents a straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93percent yield and 98percent ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives.

Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines: Via the copper-catalyzed aerobic oxygenated CC bond of indoles

Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.