942-01-8

Basic information

• Product Name: 1,2,3,4-Tetrahydrocarbazole
• Synonyms: 2,3,4,9-tetrahydro-1h-carbazol;2,3-Tetramethylene-1H-indole;5,6,7,8-tetrahydro-carbazol;5,6,7,8-Tetrahydrocarbazole;Carbazole, 1,2,3,4-tetrahydro-;Carbazole, 5,6,7,8-tetrahydro-;Tetrahydrocarbazole;AURORA 15341
• CAS NO: 942-01-8
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• EINECS: 213-385-7
• Product Categories: Building Blocks;Carbazoles;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 942-01-8.mol

Chemical Properties

• Melting Point: 118-120 °C(lit.)
• Boiling Point: 325-330 °C(lit.)
• Flash Point: 325-330°C
• Appearance: beige powder.
• Density: 1.1459 (rough estimate)
• Vapor Pressure: 0.000437mmHg at 25°C
• Refractive Index: 1.6544 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 17.84±0.20(Predicted)
• Water Solubility: Insoluble in water. Solubility in methanol (almost transparency).
• BRN: 133771
• CAS DataBase Reference: 1,2,3,4-Tetrahydrocarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydrocarbazole(942-01-8)
• EPA Substance Registry System: 1,2,3,4-Tetrahydrocarbazole(942-01-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: FE6300000
• Hazardous Substances Data: 942-01-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydrocarbazole is used as a pharmaceutical intermediate for the synthesis of various drugs and drug candidates. Its unique structure allows for the development of new and innovative therapeutic agents.
Used in Organic Synthesis:
1,2,3,4-Tetrahydrocarbazole is used as a starting material in the synthesis of various organic compounds, including:
1. Spiro[cyclopentane-1,2′-indolin-3′-one] by photooxygenation, which is a key intermediate in the development of novel pharmaceutical agents.
2. 9-Acyl-1,2,3,4-tetrahydrocarbazoles by N-acylation reactions, which can be used as precursors for the synthesis of various bioactive compounds.
3. Carbazole via palladium-catalyzed asymmetric hydrogenation reaction, which is an important intermediate in the synthesis of various organic compounds and pharmaceuticals.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 14, p. 934, 1966 DOI: 10.1248/cpb.14.934Tetrahedron Letters, 26, p. 161, 1985 DOI: 10.1016/S0040-4039(00)61869-5

InChI:InChI=1/C12H13N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1,3,5,7,13H,2,4,6,8H2

Upstream product

• 64-18-6 formic acid 
• 108-94-1 cyclohexanone 
• 100-63-0 phenylhydrazine 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 4828-96-0 cis-2,3,4,4a,9,9a-hexahydro-1H-carbazole 
• 59-88-1 phenylhydrazine hydrochloride 
• 286-20-4 cyclohexane-1,2-epoxide 
• 62-53-3 aniline 
• 615-36-1 2-bromoaniline 
• 822-87-7 2-Chlorocyclohexanone 
• 1521-51-3 rac-3-bromocyclohexene 
• 931-17-9 1,2-Cyclohexanediol 
• 79096-94-9 N-trifluoroacetyl-1,2,3,4-tetrahydrocarbazole 

Downstream Products

• 67242-61-9 1,2,3,4-tetrahydrocarbazole-9-carboxamide 
• 17017-63-9 9-benzyl-2,3,4,9-tetrahydro-1H-carbazole 
• 86844-02-2 9-phenyl-6,7,8,9-tetrahydro-5H-carbazole 
• 21144-93-4 1,2,3,4-Tetrahydro-9-carbazolyl-essigsaeure 
• 104165-41-5 9-phenylsulfonyl-2,3,4,9-tetrahydro-1H-carbazole 
• 42738-99-8 11-hydroxytetrahydrocarbazolenine 
• 78154-49-1 o-phenol 
• 4669-18-5 spiro[cyclopentane-1,2'-indolin]-3'-one 
• 18781-72-1 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole 
• 130872-84-3 C₁₉H₁₆Cl₂N₂O₂ 
• 35618-96-3 5,6,7,8-tetrahydro-carbazol-4-ol 
• 13314-76-6 1,2,3,4-tetrahydro-6-hydroxycarbazole 
• 13314-79-9 5,6,7,8-tetrahydro-carbazol-2-ol 
• 1775-86-6 5,6,7,8,8a,9-hexahydro-4bH-carbazole 

Relevant articles and documents

Formal Aza-Diels?Alder Reactions of Spiroindolenines with Electronrich Dienes

Spiroindolenines were employed as cyclic imine substrates in formal aza-Diels?Alder reactions with Danishefsky's diene or silyloxy-substituted electron-rich dienes for the synthesis of the corresponding tetrahydropyrido[1,2-a]spiroindolinones. The reactions occur under mild conditions in the presence of ytterbium triflate as Lewis acidic catalyst delivering the desired compounds in good yield. The reaction results in the preparation of a small library of a new class of conformational constrained heterocyclic derivatives that easily undergo selective and efficient manipulations.

Novel tetrahydrocarbazole benzyl pyridine hybrids as potent and selective butryl cholinesterase inhibitors with neuroprotective and β-secretase inhibition activities

Butyrylcholinesterase (BuChE) inhibitors have become interesting target for treatment of Alzheimer's disease (AD). A series of dual binding site BuChE inhibitors were designed and synthesized based on 2,3,4,9-tetrahydro-1H-carbazole attached benzyl pyridine moieties. In-vitro assay revealed that all of the designed compounds were selective and potent BuChE inhibitors. The most potent BuChE inhibitor was compound 6i (IC50 = 0.088 ± 0.0009 μM) with the mixed-type inhibition. Docking study revealed that 6i is a dual binding site BuChE inhibitor. Also, Pharmacokinetic properties for 6i were accurate to Lipinski's rule. In addition, compound 6i demonstrated neuroprotective and β-secretase (BACE1) inhibition activities. This compound could also inhibit AChE-induced and self-induced Aβ peptide aggregation at concentration of 100 μM and 10 μM respectively. Generally, the results are presented as new potent selective BuChE inhibitors with a therapeutic potential for the treatment of AD.

13C NMR Chemical Shift Assignments for Some Carbazole Derivatives

13C NMR chemical shift assignments have been made for a series of 1-substituted carbazoles, 8-substituted 1,2,3,4-tetrahydrocarbazoles, 1-substituted benzocarbazoles and 6-substituted dibenzocarbazoles.Single examples were examined of other classes of substituted carbazoles: 3-butylcarbazole and its tetrahydro precursor 6-butyl-1,2,3,4-tetrahydrocarbazole, 8-butyl- and 8,10-diethylbenzocarbazoles and their 5,6-dihydro precursors, dibenzocarbazole and its 5,6,7,8-tetrahydro precursor, benzocarbazole and its 6-chloro derivatives and 5,6-dihydrobenzocarbazole and 5,6,8,9-tetrahydrodibenzocarbazole and their N-methyl derivatives.In addition, the N-(1-pyrrolidinomethyl) derivatives of carbazole, 1,2,3,4-tetrahydrocarbazole, benzocarbazole and dibenzocarbazole were also studied.KEY WORDS 13C NMR Chemical shift assignments Carbazole derivatives.

Fischer indole synthesis over hydrous zirconia-supported niobium oxide

Supported niobium oxides are investigated as green catalysts for Fischer indole reaction. By means of wet impregnation, 1040 wt-% Nb2O 5 were loaded onto hydrous zirconia as a support. Pore size distribution curves showed that the niobium oxide overlayer was uniformly dispersed onto the mesoporous support. Samples with close to a monolayer coverage of niobium oxide had the highest activity in the Fischer indole reaction of phenylhydrazine with both 3-heptanone and cyclohexanone. A coverage higher than a monolayer led to lower activity. In comparison, the supported catalysts were more active than bulk niobium oxide or a sample prepared by co-precipitation of hydrous zirconia and niobium oxide. CSIRO 2009.

Tetrahydrocarbazoles by mechanochemical Fischer indolisation

The Fischer indolisation (FI) typically proceeds in the presence of a Br?nsted or Lewis acid in an organic solvent at elevated temperatures. Herein, we report that tetrahydrocarbazoles (THCs) are accessible by mechanochemical FI at ambient temperature. Using phenylhydrazine hydrochlorides in the presence of silica is critical for this solid-state variant of the FI.

Palladium-catalyzed dearomative allylation of indoles with cyclopropyl acetylenes: access to indolenine derivatives

A palladium-catalyzed redox-neutral allylic alkylation of indoles with cyclopropyl acetylenes has been disclosed. Various 1,3-diene indolenine framework bearing a quaternary stereocenter at the C3 position were synthesized straightforwardly in good to excellent yields with high regio- and stereoselectivities. The reaction could be further expanded to the dearomatization of naphthols to synthesize functionalized cyclohexadienones with 1,3-diene motifs. The reaction exhibited high atom economy and good functional group tolerance.

One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles

A one-pot, three-component protocol for the synthesis of 1,2,3-trisubstituted indoles has been developed, based upon a Fischer indolisation-indoleN-alkylation sequence. This procedure is very rapid (total reaction time under 30 minutes), operationally straightforward, generally high yielding and draws upon readily available building blocks (aryl hydrazines, ketones, alkyl halides) to generate densely substituted indole products. We have demonstrated the utility of this process in the synthesis of 23 indoles, benzoindoles and tetrahydrocarbazoles bearing varied and useful functionality.

Synthesis of indoles through acceptorless dehydrogenative coupling catalyzed by nickel on silica-alumina

The high atom-economical formation of indoles from anilines and diols was described with affordable and easy to handle Ni/SiO2-Al2O3. After optimization, 2,3-dimethylindole was isolated with an excellent 98% yield in neat conditions. The scope of the reaction was studied and 13 indoles were isolated in 16–80% yields.

Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines

The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.

Iron-Catalyzed Radical Activation Mechanism for Denitrogenative Rearrangement Over C(sp3)–H Amination

An iron-catalyzed denitrogenative rearrangement of 1,2,3,4-tetrazole is developed over the competitive C(sp3)–H amination. This catalytic rearrangement reaction follows an unprecedented metalloradical activation mechanism. Employing the developed method, a wide number of complex-N-heterocyclic product classes have been accessed. The synthetic utility of this radical activation method is showcased with the short synthesis of a bioactive molecule. Collectively, this discovery underlines the progress of radical activation strategy that should find wide application in the perspective of medicinal chemistry, drug discovery and natural product synthesis research.