132906-53-7

Basic information

• Product Name: 8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one
• Synonyms: 8-bromo-1,2,3,4-tetrahydro-9H-carbazol-1-one
• CAS NO: 132906-53-7
• Molecular Formula: C₁₂H₁₀BrNO
• Molecular Weight: 264.1179
• Mol File: 132906-53-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 164-165 °C
• Boiling Point: 437.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.636±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.47±0.20(Predicted)
• CAS DataBase Reference: 8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one(132906-53-7)
• EPA Substance Registry System: 8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one(132906-53-7)

Safety Data

• Hazardous Substances Data: 132906-53-7(Hazardous Substances Data)

Usage

General Description

8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one is a chemical compound that belongs to the class of carbazoles, which are organic heterocyclic compounds. It is derived from carbazole through bromination and the addition of a ketone group. The presence of a bromine atom and a carbonyl group can potentially impart specific chemical and biological properties to this compound. Carbazoles have been investigated for various applications, including pharmaceuticals, agrochemicals, and materials science. The specific properties and potential applications of 8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one would depend on further studies and evaluations.

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Relevant articles and documents

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Design, synthesis and evaluation of hybrid of tetrahydrocarbazole with 2,4-diaminopyrimidine scaffold as antibacterial agents

Several 6-substituted tetrahydrocarbazole derivatives were designed, synthesized and evaluated for the antibacterial activities against Staphylococcus aureus Newman strain. Subsequently, 2,4-diaminopyrimidine scaffold was merged with the tetrahydrocarbazole unit to generate a series of novel hybrid derivatives and the antibacterial activities were also investigated. Among these novel hybrids, compound 12c showed the most potent activity with a MIC of 0.39–0.78 μg/mL against S. aureus Newman and Escherichia coli AB1157 strain. In addition, compound 12c exhibited low MIC values against a panel of multidrug-resistant strains of S. aureus.

Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation

A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF3)2 (PIFA), through a direct intramolecular oxidative C(sp2)-C(sp2) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.