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

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

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 
• 75-01-4 chloroethylene 
• 51050-85-2 1-vinyl-4,5,6,7-tetrahydroindole 
• 74-86-2 acetylene 
• 23456-78-2 1,4,5,6-tetrahydro-7H-indol-7-one 
• 51534-73-7 2-(2-oxocyclohexyl)acetaldehyde 
• 50553-03-2 O-(2-hydroxy-ethyl)-cyclohexanone oxime 
• 2380-94-1 1H-indol-4-ol 
• 85696-95-3 1-methyl-1H-indol-4-amine 
• 106-93-4 ethylene dibromide 
• 107-06-2 1,2-dichloro-ethane 
• 120256-10-2 1-(dimethylamino)-4,5,6,7-tetrahydro-1H-indole 

Downstream Products

• 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.

Reduction of the indole ring system: Synthesis of 4,5,6,7-tetrahydroindoles

A general two-step procedure for the reduction of indoles to the corresponding 4,5,6,7-tetrahydroindoles has been developed. A regioselective Birch reduction followed by catalytic hydrogenation is employed to accomplish this transformation. Yields for the sensitive pyrrole products are typically between 40 and 50%. This method provides access to complex chiral pyrroles that cannot be readily prepared by other methods.

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.

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 %.

Preparation of cyclic prodiginines by mutasynthesis in pseudomonas putida kt2440

Prodiginines are a group of naturally occurring pyrrole alkaloids produced by various microorganisms and known for their broad biological activities. The production of nature-inspired cyclic prodiginines was enabled by combining organic synthesis with a mutasynthesis approach based on the GRAS (generally recognized as safe) certified host strain Pseudomonas putida KT2440. The newly prepared prodiginines exerted antimicrobial effects against relevant alternative biotechnological microbial hosts whereas P. putida itself exhibited remarkable tolerance against all tested prodiginines, thus corroborating the bacterium’s exceptional suitability as a mutasynthesis host for the production of these cytotoxic secondary metabolites. Moreover, the produced cyclic prodiginines proved to be autophagy modulators in human breast cancer cells. One promising cyclic prodiginine derivative stood out, being twice as potent as prodigiosin, the most prominent member of the prodiginine family, and its synthetic derivative obatoclax mesylate.

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

STABILIZATION OF ACTIVE METAL CATALYSTS AT METAL-ORGANIC FRAMEWORK NODES FOR HIGHLY EFFICIENT ORGANIC TRANSFORMATIONS

Metal-organic framework (MOFs) compositions based on post?synthetic metalation of secondary building unit (SBU) terminal or bridging OH or OH2 groups with metal precursors or other post-synthetic manipulations are described. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations, including the regioselective boryiation and siiylation of benzyiic C—H bonds, the hydrogenation of aikenes, imines, carbonyls, nitroarenes, and heterocycles, hydroboration, hydrophosphination, and cyclization reactions. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

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.

Isothiourea-catalysed enantioselective pyrrolizine synthesis: Synthetic and computational studies

The catalytic enantioselective synthesis of a range of cis-pyrrolizine carboxylate derivatives with outstanding stereocontrol (14 examples, >95:5 dr, >98:2 er) through an isothiourea-catalyzed intramolecular Michael addition-lactonisation and ring-opening

Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids

A facile one-pot approach based on a thermally induced metal- and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina- and Lycorine-type alkaloids, namely (±)-erysotramidine, (±)-erysotrine, (±)-erythravine, (±)-γ-lycorane, and abnormal erythrinanes (±)-coccoline and (±)-coccuvinine.