14192-67-7

Basic information

• Product Name: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE
• Synonyms: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE;CHEMBRDG-BB 6043153;TIMTEC-BB SBB014433;6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one(SALTDATA: FREE)
• CAS NO: 14192-67-7
• Molecular Formula: C₁₂H₁₀ClNO
• Molecular Weight: 219.67
• Mol File: 14192-67-7.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 417.7 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: /
• Density: 1.397 g/cm³
• Vapor Pressure: 3.47E-07mmHg at 25°C
• Refractive Index: 1.694
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE(14192-67-7)
• EPA Substance Registry System: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE(14192-67-7)

Safety Data

• Hazardous Substances Data: 14192-67-7(Hazardous Substances Data)

Usage

Description

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is a chemical compound that belongs to the carbazole class, characterized by its white to off-white solid appearance and a molecular formula of C13H10ClNO. It is known for its potential applications in various fields, including pharmaceuticals, organic electronics, and as an antitumor agent, due to its electronic, optical properties, and ability to inhibit cancer cell growth.

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is used as a building block for the synthesis of various pharmaceutical drugs and agrochemicals, contributing to the development of new therapeutic agents and agricultural products.
Used in Organic Electronic Materials:
In the field of organic electronic materials, 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is utilized for its electronic and optical properties, which make it a valuable component in the creation of advanced electronic devices and systems.
Used in Antitumor Research:
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is studied for its potential as an antitumor agent, given its ability to inhibit the growth of cancer cells, offering a promising avenue for cancer treatment and therapeutic development.

InChI:InChI=1/C12H10ClNO/c13-7-4-5-10-9(6-7)8-2-1-3-11(15)12(8)14-10/h4-6,14H,1-3H2

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Downstream Products

• 156424-67-8 6-chloro-1-hydroxyimino-1,2,3,4-tetrahydrocarbazole 
• 121594-06-7 [6-Chloro-2,3,4,9-tetrahydro-carbazol-(1E)-ylidene]-(2-phenoxy-ethyl)-amine 
• 1612188-90-5 2-amino-8-chloro-4-(4'-dimethylamino-phenyl)-5,6-dihydro-11H-benzo[a]carbazole-1,3-dicarbonitrile 
• 1612188-89-2 2-amino-8-chloro-4-(4'-bromo-phenyl)-5,6-dihydro-11H-benzo[a]carbazole-1,3-dicarbonitrile 
• 1612188-88-1 2-amino-8-chloro-4-phenyl-5,6-dihydro-11H-benzo[a]carbazole-1,3-dicarbonitrile 

Relevant articles and documents

Reactions of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates. Synthesis of methyl isoxazolo[5,4-a]carbazole-3-carboxylates

The reaction of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates (1a-e) with hydroxylamine hydrochloride in alcoholic KOH afforded 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles (2a-e), and in acetic acid methyl isoxazolo[5,4-a]carbazole-3-carboxylates (3a-e). Ketoesters 1a-e with urea and thiourea under acidic conditions yielded a mixture of the respective 1-hydroxycarbazoles (6a-e) and 2,3,4,9-tetrahydro-1H-carbazol-1-ones (7a-e), but under basic conditions the respective 1-carbimido-and 1-thiocarbimido-2,3,4,9- tetrahydro-1H-carbazoles (8a-e and 9a-e) were formed. Plausible mechanisms are proposed.

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.

1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF

The present invention relates to 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole derivative compounds and uses thereof. In particular, compounds of the invention have antibacterial activity and/or are capable of re-sensitizing methicillin-resistant Staphylococcus aureus to a P-lactam antibiotic or a combination of a P-lactam antibiotic and a P-lactamase inhibitor. The present invention also relates to a method for producing and using said compounds.

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.