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

Uses

Different sources of media describe the Uses of 13618-91-2 differently. You can refer to the following data:
1. 4,5,6,7-Tetrahydro-1H-indole is used in preparation of chiral tetraaryl-substituted Methane. Also, used in preparation of 4-substituted Phenylamidine derivatives used for controlling phytopathogenic microorganisms.
2. 4,5,6,7-Tetrahydroindole was used as reactant in:synthesis of ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)-2-propynoatepreparation of BODIPY dyesN-alkylation with chloromethyloxiranepreparation of hydroindolepropynoate by chemo- and regioselective solvent-free ethynylationpalladium- and copper-free cross-coupling of halopropynoatespreparation of carbonylalkenyl indoles via coupling with dicarbonyl compounds1:2 annelation of 4,5,6,7-tetrahydroindole with 1-benzoyl-2-phenylacetylene

General Description

4,5,6,7-Tetrahydroindoles, due to their easy aromatization, are good intermediates to synthesize indoles. 4,5,6,7-Tetrahydroindole on condensation with cyanoacetate leads to 1-ethylthio-2-cyano-4,5,6,7-tetrahydrocyclohexa-[c]-3H-pyrrolizin-3-one.

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

Upstream product

• 100-64-1 cyclohexanone-oxime 
• 593-60-2 Vinyl bromide 
• 107-06-2 1,2-dichloro-ethane 
• 120-72-9 indole 
• 56671-28-4 4,5,6,7-tetrahydro-4-oxobenzofuran-3-carboxylic acid 
• 108-94-1 cyclohexanone 
• 504-02-9 1,3-cylohexanedione 
• 128428-59-1 3-hydroxy-4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-3-carboxylic acid ethyl ester 
• 120256-04-4 N'-[2-[1,3]Dioxolan-2-ylmethyl-cyclohex-(E)-ylidene]-N,N-dimethyl-hydrazine 
• 10424-93-8 N'-cyclohexylidene-N,N-dimethyl-hydrazine 
• 147329-74-6 2-(2-Bromo-1-ethoxy-ethyl)-cyclohexanone 
• 50553-03-2 O-(2-hydroxy-ethyl)-cyclohexanone oxime 
• 176097-78-2 3a,7,7-trichloro-3,3a,4,5,6,7-hexahydro-2H-indole 
• 18159-32-5 Δ¹⁽⁸⁾-hexahydroindole 

Downstream Products

• 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.