21865-50-9

Basic information

• Product Name: 6-bromo-2,3,4,9-tetrahydro-1H-carbazole
• Synonyms: 6-bromo-2,3,4,9-tetrahydro-1H-carbazole;2-broMo-5,6,7,8,9,10-hexahydrocyclohepta[b]indole;6-BROMO-1,2,3,4-TETRAHYDROCARBAZOLE
• CAS NO: 21865-50-9
• Molecular Formula: C₁₂H₁₂BrN
• Molecular Weight: 250.15
• Mol File: 21865-50-9.mol

Chemical Properties

• Melting Point: 151.5-152.0 °C
• Boiling Point: 378.7 °C at 760 mmHg
• Flash Point: 182.8 °C
• Appearance: /
• Density: 1.516 g/cm³
• Vapor Pressure: 1.34E-05mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.88±0.20(Predicted)
• CAS DataBase Reference: 6-bromo-2,3,4,9-tetrahydro-1H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-2,3,4,9-tetrahydro-1H-carbazole(21865-50-9)
• EPA Substance Registry System: 6-bromo-2,3,4,9-tetrahydro-1H-carbazole(21865-50-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 21865-50-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-bromo-2,3,4,9-tetrahydro-1H-carbazole is used as a potential drug candidate for the development of new medications due to its unique chemical structure and properties. It is particularly considered for the treatment of neurological disorders, given its potential to interact with specific biological targets and pathways.
Used in Medicinal Chemistry:
6-bromo-2,3,4,9-tetrahydro-1H-carbazole serves as a building block in the synthesis of other biologically active compounds. Its chemical properties allow it to be modified and incorporated into various drug molecules, enhancing their therapeutic effects and selectivity.
Used in Research and Development:
6-bromo-2,3,4,9-tetrahydro-1H-carbazole is an important target for further research and development in the field of medicinal chemistry. Its unique structure and potential pharmaceutical uses make it a valuable compound for exploring new drug discovery approaches and understanding its mechanism of action in treating various diseases.

InChI:InChI=1/C12H12BrN/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h5-7,14H,1-4H2

Upstream product

• 108-94-1 cyclohexanone 
• 1215-42-5 1,2-bis(4-bromophenyl)diazene oxide 
• 1601-98-5 1,2-bis(4-bromophenyl)diazene 
• 106-40-1 4-bromo-aniline 
• 110-52-1 1,4-dibromo-butane 
• 10075-50-0 5-bromo-1H-indole 
• 92644-16-1 tert-butyl 2-(p-bromophenyl)hydrazine-1-carboxylate 
• 41931-18-4 (4-bromophenyl)hydrazine hydrochloride salt 
• 108-85-0 1-bromocyclohexane 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 589-21-9 (4-bromophenyl)hydrazine 
• 117489-28-8 1-(4-bromophenyl)-2-cyclohexylidenehydrazine 
• 100116-02-7 2-(4-bromo-anilino)-cyclohexanone 

Downstream Products

• 59514-18-0 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 893409-97-7 4-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-ylamino)benzonitrile 
• 1423039-54-6 3-(4a-allyl-2,3,4,4a-tetrahydro-1H-carbazol-6-yl)benzonitrile 
• 1423039-52-4 4a-allyl-6-(2,6-dimethylphenyl)-2,3,4,4a-tetrahydro-1H-carbazole 
• 1423039-50-2 4a-allyl-6-(2-fluorophenyl)-2,3,4,4a-tetrahydro-1H-carbazole 
• 1423039-49-9 4a-allyl-6-(4-(trifluoromethyl)phenyl)-2,3,4,4a-tetrahydro-1H-carbazole 
• 1423039-46-6 4a-allyl-6-phenyl-2,3,4,4a-tetrahydro-1H-carbazole 
• 1313809-70-9 6-bromo-9-(4-methoxybenzyl)-1,2,3,4-tetrahydro-9H-carbazole 
• 1313809-59-4 6-bromo-1-methoxy-9-(4-methoxybenzyl)-1,2,3,4-tetrahydro-9H-carbazole 
• 1181975-28-9 6-bromo-9-(3-(3,5-difluorophenoxy)propyl)-2,3,4,9-tetrahydro-1H-carbazole 
• 1181975-27-8 6-bromo-9-(3-(3,5-dimethylphenoxy)propyl)-2,3,4,9-tetrahydro-1H-carbazole 
• 1592-95-6 3-bromo-9H-carbazole 
• 18992-85-3 3-methoxycarbazole 
• 859805-93-9 (+/-)-6-bromo-(4ar,9ac)-1,2,3,4,4a,9a-hexahydro-carbazole 

Relevant articles and documents

Traceless Fischer indole synthesis on the solid phase

The Fischer indole synthesis using polymer-bound hydrazines is employed as the key step for the development of a traceless indole synthesis on a solid support.

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

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.

Aromatic compound and organoelectro　luminescent device comprising the compound

The present invention relates to an aromatic compound denoted by chemical formula 1, and an organic electroluminescent device comprising the compound. The organic electroluminescent device comprising the aromatic compound by the present invention has low driving voltage, and excellent lifetime properties and luminance efficiency.

An electroluminescent compound and an electroluminescent device comprising the same

The present invention relates to an organic light-emitting compound represented by [Chemical formula 1]. An organic electroluminescent device comprising the organic light-emitting compound in the present invention has excellent power efficiency, light-emitting efficiency, and long life cycle because the present invention can be operated by a lower driving-voltage in comparison with a device comprising conventional phosphorescent host materials. [Chemical formula 1].

Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade

Employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles was probed in the presence of PdCl 2 (MeCN) 2 as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles from indoles (11 examples, 31-68% yield). Seven-membered-ring annulation was feasible by an initial coupling at positon C2 followed by alkylation at C3.

Heterocyclic com pounds and organic light-emitting diode including the same

PURPOSE: A heterocyclic compound and an organic electroluminescent device containing the same are provided to show stability and superior light emitting properties such as low driving voltage or current efficiency. CONSTITUTION: A heterocyclic compound is denoted by chemical formula 1. An organic electroluminescent device comprises an anode, a cathode, and layers containing the heterocyclic compounds, which are placed between the anode and the cathode. A light emitting layer between the anode and the cathode contains the heterocyclic compounds. The organic electroluminescent device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

Synthesis and evaluation of indole derivatives as photosynthesis and plant growth inhibitors

Indole derivatives were synthetized based on the Fischer indole methodology using different phenyl hydrazine hydrochlorides and either cyclohexanone or 2-butanone. The pre- and post-emergent herbicidal activities were evaluated against Ipomoea grandifolia. A carbazole, 6-chloro-2,3,4,9-tetrahydro-1H-carbazole (3b), decreased the PIabs parameter by 32% and increased the cross-section related parameters, indicating the inactivation of the reaction center on photosystem II. Compound 3b acts as a post-emergent herbicide prototype since dry biomass was reduced by 50%, corroborating the fluorescence results. Comparing instead with a germination experiment, 2,3,4,9-tetrahydro-1H-carbazole (3a) was found to be the most effective agent, inhibiting seed germination by 22% and decreasing root length by 50%. The tetrahydrocarbazoles showed better results than indole derivatives potentially due to the presence of methylene groups at structures, which increase the compounds' lipophilicity and may facilitate their access to the plant. In addition, electron withdrawing groups on the aromatic ring were found to correlate with increased herbicide activity. Further optimization of this series towards the development of herbicides is ongoing.

Heterocyclic com pounds and organic light-emitting diode including the same

The present invention relates to novel heterocyclic compounds of chemical formula 1 and an organic electroluminescent device containing the same as a light emitting material and, more specifically, to stable heterocyclic compounds with superior light emitting properties such as driving voltage and light emitting efficiency; and an organic electroluminescent device containing the same. Also, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and layers which are inserted between the anode and the cathode and contain the heterocyclic compounds of chemical formula 1.

Aromatic compound and organoelectroluminescent device comprising the compound

The present invention relates to a novel aromatic compound and an organic electroluminescent device comprising the same. The present invention relates to an organic electroluminescent device including an aromatic compound. (by machine translation)