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

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

Uses

Used in Pharmaceutical Applications:
8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one is used as a potential pharmaceutical agent for its possible biological activities. The bromine atom and carbonyl group may contribute to its interaction with biological targets, making it a candidate for further research in drug development.
Used in Agrochemical Applications:
8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one is used as a potential agrochemical compound for its possible pesticidal or herbicidal properties. The specific chemical structure may allow it to interact with pests or weeds in a way that could be harnessed for agricultural purposes.
Used in Materials Science Applications:
8-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one is used as a potential material in materials science for its possible properties in areas such as electronics, optics, or polymers. The bromine and carbonyl groups may influence its electronic, optical, or structural characteristics, making it a candidate for further exploration in material development.

Upstream product

• 50709-33-6 2-bromophenylhydrazine hydrochloride 
• 6946-05-0 2-aminocyclohexanone hydrochloride 
• 108-94-1 cyclohexanone 
• 27372-41-4 8-bromo-2,3,4,9-tetrahydro-1H-carbazole 
• 765-87-7 cyclohexane-1,2-dione 
• 16732-66-4 2-bromophenylhydrazine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 141091-37-4 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 89490-05-1 cyclohex-1-enylboronic acid 
• 1071035-81-8 2-((2-bromophenyl)amino)cyclohex-2-enone 
• 615-36-1 2-bromoaniline 
• 23740-64-9 2-morpholinocyclohex-2-enone 
• 132906-49-1 ortho-bromophenylhydrazone 

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.

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an anim

Synthesis of tricyclic units of indole alkaloids: Application of Fischer indolization and olefin metathesis

Simple synthetic approaches to pyridocarbazole and azepinocarbazole derivatives have been reported via Fischer indolization, Grignard reaction and olefin metathesis as key steps. In addition, a combination Sonogashira coupling and Pauson-Khand reaction has been used to assemble extended pyridocarbazole derivative.

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.

Convenient and efficient synthesis of 1-oxo-1,2,3,4-tetrahydrocarbazoles via Fischer indole synthesis

A convenient synthesis of 1-oxo-1,2,3,4-tetra-hydrocarbazoles has been developed by reaction of 2-aminocyclohexanone hydrochlorides with various phenylhydrazine hydrochlorides via Fischer indole synthesis under mild conditions. The method is more satisfac