13618-91-2

Basic information

• Product Name: 4,5,6,7-TETRAHYDROINDOLE
• Synonyms: 4,5,6,7-TETRAHYDROINDOLE;4,5,6,7-TETRAHYDRO-1H-INDOLE;4,5,6,7-TETRAHYDROINDOLE 98+%;1H-Indole, 4,5,6,7-tetrahydro-;2,3-Tetramethylenepyrrole;Cyclohex[b]pyrrole;NSC 122455;4,5,6,7-Tetrahydroindole 98%
• CAS NO: 13618-91-2
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 13618-91-2.mol
• Article Data: 37

Chemical Properties

• Melting Point: 53-57 °C(lit.)
• Boiling Point: 253.3 °C at 760 mmHg
• Flash Point: 101.4 °C
• Appearance: /
• Density: 1.057g/cm³
• Vapor Pressure: 0.0293mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• BRN: 108853
• CAS DataBase Reference: 4,5,6,7-TETRAHYDROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6,7-TETRAHYDROINDOLE(13618-91-2)
• EPA Substance Registry System: 4,5,6,7-TETRAHYDROINDOLE(13618-91-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 13618-91-2(Hazardous Substances Data)

Usage

Description

4,5,6,7-Tetrahydroindole (THI) is an organic compound with the molecular formula C8H11N. It is a reduced form of indole, a heterocyclic aromatic organic compound that contains a pyrrole fused to a benzene ring. THI is known for its easy aromatization, making it a versatile intermediate in the synthesis of various indole derivatives.

Uses

Used in Pharmaceutical Industry:
4,5,6,7-Tetrahydroindole is used as a key intermediate for the synthesis of chiral tetraaryl-substituted methane, which are important in the development of pharmaceutical compounds due to their unique structural properties and potential applications in drug design.
Used in Agricultural Industry:
4,5,6,7-Tetrahydroindole is used as a reactant in the preparation of 4-substituted phenylamidine derivatives, which are utilized for controlling phytopathogenic microorganisms. These derivatives can help in the development of new pesticides or fungicides to protect crops from diseases.
Used in Chemical Synthesis:
4,5,6,7-Tetrahydroindole is employed in various chemical reactions, including:
Synthesis of ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)-2-propynoate
Preparation of BODIPY dyes, which are widely used in bioimaging and as fluorescent markers
N-alkylation with chloromethyloxirane, a reaction that introduces an alkyl group to the nitrogen atom of the indole ring
Preparation of hydroindolepropynoate by chemoand regioselective solvent-free ethynylation
Palladiumand copper-free cross-coupling of halopropynoates, which allows for the formation of new carbon-carbon bonds in the molecule
Preparation of carbonylalkenyl indoles via coupling with dicarbonyl compounds, which can lead to the synthesis of complex indole-based structures
1:2 Annelation of 4,5,6,7-tetrahydroindole with 1-benzoyl-2-phenylacetylene, a reaction that involves the formation of a new ring structure in the molecule

InChI:InChI=1/C8H11N/c1-2-4-8-7(3-1)5-6-9-8/h5-6,9H,1-4H2

Upstream product

• 56671-28-4 4,5,6,7-tetrahydro-4-oxobenzofuran-3-carboxylic acid 
• 100-64-1 cyclohexanone-oxime 
• 593-60-2 Vinyl bromide 
• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 
• 75-01-4 chloroethylene 
• 51050-85-2 1-vinyl-4,5,6,7-tetrahydroindole 
• 132065-70-4 C₈H₁₃NS 
• 120256-10-2 1-(dimethylamino)-4,5,6,7-tetrahydro-1H-indole 
• 107-06-2 1,2-dichloro-ethane 
• 106-93-4 ethylene dibromide 
• 74-86-2 acetylene 
• 23456-78-2 1,4,5,6-tetrahydro-7H-indol-7-one 
• 120-72-9 indole 
• 51534-73-7 2-(2-oxocyclohexyl)acetaldehyde 

Downstream Products

• 104165-42-6 4,5,6,7-tetrahydro-1-(phenylsulfonyl)indole 
• 2720-67-4 potassium propylxanthate 
• 120-72-9 indole 
• 80744-01-0 4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde 
• 634892-64-1 1-isopropenyl-4,5,6,7-tetrahydro-1H-indole 

Relevant articles and documents

CYCLOALKAPYRROLES FROM KETOXIMES AND ACETYLENE: SYNTHESIS AND KINETIC INVESTIGATION

The rate constants of formation of cycloalkapyrroles and their N-vinyl derivatives were determined, and it was shown that efficient preparation of pyrroles condensed with aliphatic macrocycles from the corresponding ketoximes and acetylene in the KOH-DMSO system is possible.

Effect of alkali metal cations on the synthesis of 4,5,6,7-tetrahydroindole and its vinyl derivative from cyclohexanone oxime and acetylene in MOH-DMSO systems

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A new approach for the synthesis of 2-substituted indole derivatives via Michael type adducts

4,7-Dihydroindole undergoes regioselective alkylation at the 2-position of the indole nucleus through conjugate addition with α,β-unsaturated carbonyl compounds. The oxidation of the Michael adducts affords the corresponding 2-substituted indole derivatives which were characterized by spectroscopic methods.

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Highly efficient one-pot multi-directional selective hydrogenation and N-alkylation catalyzed by Ru/LDH under mild conditions

Atomic economy, non-toxicity, harmlessness and multidirectional selectivity advocated by green chemistry have increasingly become a hot and difficult research topic. Herein, we present a highly efficient, one-pot tandem and easy-to-operate method through which we could directly produce a broad range of multi-directional selective hydrogenated amines or N-alkyl aliphatic amines using aromatic nitro compounds as raw materials. Ru/LDH with characteristics of layered mesoporous structure, well dispersed small Ru nanoparticles and LDH stabilization to the Ru NPs was employed as the catalyst. It is remarkable that multi-directional superb chemoselectivity to aromatic amines, alicyclic amines as well as N-alkyl aliphatic amines could be achieved with excellent catalytic activity and recyclability by tuning reaction conditions over 5wt%Ru/LDH-2. Additionally, this catalytic system also exhibited attractive activity and multi-directional chemoselectivity in the hydrogenation of quinoline and its derivatives with solvents of different polarity. Chemoselectivity to 5,6,7,8-tetrahydroquinoline derivatives could reach as high as 95.6 %.

Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY

The boron-dipyrromethene (BODIPY) dye containing an annelated cyclohexyl rings at the 2,3 and 5,6-positions of pyrroles has been synthesized and characterized. Photochemical properties of the obtained compound have been investigated in different individua

Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids

N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1-3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs). Particularly a diol-functionalised IL shows the best performance in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline (1THQ) with up to 99% selectivity.