1484-05-5

Usage

Uses

Used in Organic Synthesis:
1-(9-Methyl-9H-carbazol-3-yl)-ethanone is used as a building block in the synthesis of various organic compounds due to its reactive ketone group and the presence of the carbazole moiety, which can be further functionalized to create a wide range of chemical products.
Used in Chemistry and Materials Science:
In the field of chemistry and materials science, 1-(9-Methyl-9H-carbazol-3-yl)-ethanone is utilized for its ability to form new compounds with potential applications in areas such as organic light-emitting diodes (OLEDs), photovoltaics, and other advanced materials.
Used in Pharmaceutical Research:
1-(9-Methyl-9H-carbazol-3-yl)-ethanone may have potential uses in pharmaceutical research as its unique structure and properties could be harnessed to develop new drugs or drug candidates. The carbazole core is known to exhibit a range of biological activities, and the addition of the ketone group could provide new avenues for drug design and optimization.
Used in Solvent Systems:
Due to its solubility in organic solvents, 1-(9-Methyl-9H-carbazol-3-yl)-ethanone can be used in solvent systems for various chemical reactions, facilitating the synthesis of complex organic molecules and improving reaction yields and selectivity.

InChI:InChI=1/C15H13NO/c1-10(17)11-7-8-15-13(9-11)12-5-3-4-6-14(12)16(15)2/h3-9H,1-2H3

Upstream product

• 1484-12-4 N-methylcarbazole 
• 75-36-5 acetyl chloride 
• 86-74-8 9H-carbazole 
• 574-39-0 9-acetylcarbazole 
• 108-24-7 acetic anhydride 
• 38292-40-9 1,2-dimethyl-1H-indole-3-carbaldehyde 
• 78-94-4 methyl vinyl ketone 
• 3215-37-0 3-acetylcarbazole 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1449676-63-4 4-methyl-N′-(1-(9-methyl-9H-carbazol-3-yl)ethylidene)benzenesulfonohydrazide 
• 1372602-87-3 3-(1-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)ethyl)-9-methyl-9H-carbazole 
• 1372602-86-2 9-methyl-3-(1-(4-(2-nitrophenyl)-1H-1,2,3-triazol-1-yl)ethyl)-9Hcarbazole 
• 1372602-85-1 3-(1-(4-(benzyloxymethyl)-1H-1,2,3-triazol-1-yl)ethyl)-9-methyl-9H-carbazole 
• 1372602-80-6 9-methyl-3-(1-(4-phenyl-1H-1,2,3-triazol-1-yl)ethyl)-9H-carbazole 

Relevant academic research and scientific papers

Anionic Cycloaddition Reactions Of Indole-2,3-dienolate With Dienophiles: A Facile Regiospecific Route To Substituted Carbazoles

Indole 2,3-dienolate derived by deprotonation of 1,2-dimethylindole-3-carboxaldehyde is shown to be useful 1,4-dipole synthon (anionic indolo-2,3-quinodimethane) which undergoes facile cycloaddition with wide range of dienophiles affording substituted car

Structure-reactivity relationship of probes based on the H2S-mediated reductive cleavage of the CC bond

Recently, we discovered the H2S-mediated reductive cleavage of the CC bond, and applied this reaction to design probes for the detection of H2S. To extensively elucidate the structure-reactivity relationship, our current work further investigated the effect of substitutes that connected to the CC bond on the H2S-mediated reductive cleavage, wherein different kinds of electron-withdrawing groups (such as pyridine, bipyridine, terpyridine) and electron donating groups (such as carbazole, N,N-dimethylaniline and phenothiazine) were conjugated to the CC bond of interest. Experimental results and DFT calculations showed that the strength of the electron-donating and withdrawing substitutes could significantly affect the reductive cleavage of the CC bond. Unexpectedly, the reductive cleavage was not influenced by the change of the C(2) and C(3) positions in phenothiazine. On this basis, two probes (NPTZ-P1 and NPTZ-P2) with a C(3)-substituted phenothiazine were thus developed and successfully applied for sensing exogenous H2S in living HeLa cells, which implied their potential in bioimaging. This study provides further understanding on the structure-reactivity relationship of the H2S-mediated reductive cleavage of the CC bond, and is also valuable for exploring new reactions of the CC bond in organic synthesis. This journal is

A Green Synthesis of 2-Amino-4-(9H-carbazole-3-yl)thiophene-3-carbonitriles by a Step-wise and One-pot Three-component Gewald Reaction

An eco-friendly method has been developed for the synthesis of 2-amino-4-(9H-carbazole-3-yl)thiophene-3-carbonitriles from preliminary carbazole (1) through an intermediate of 2-(1-(9H-carbazole-3-yl)ethylidene)malononitriles using the Knoevenagel condensation followed by the Gewald reaction. On the other hand, the target compounds could also be prepared in a one-pot three-component manner by treating equimolar quantities of 1-(9H-carbazole-3-yl)ethanone (3), malononitrile, and elemental sulfur. The merits of this preparation are mild reaction conditions. The Gewald reaction is executed with inorganic base NaHCO3 (H2O) in tetrahydrofuran, easy work-up procedure with good yields.

A general synthesis of arylindoles and (1-arylvinyl)carbazoles: Via a one-pot reaction from N -tosylhydrazones and 2-nitro-haloarenes and their potential application to colon cancer

A convergent and effective synthesis of 3-aryl-indoles, 2,3-diaryl indoles, and (1-arylvinyl)carbazoles from a one-pot sequence involving the coupling of N-tosylhydrazones with ortho-nitro-haloarenes followed by a cyclization has been developed. Compound 5i exhibits excellent antiproliferative activity in the low nM range against colon cancer cell lines.

Design, synthesis, and structure-activity correlations of novel dibenzo[b,d furan, dibenzo[b,d]thiophene, and N-methylcarbazole clubbed 1,2,3-triazoles as potent inhibitors of mycobacterium tuberculosis

A molecular hybridization approach is an emerging structural modification tool to design new molecules with improved pharmacophoric properties. In this study, 1,2,3-triazole-based Mycobacterium tuberculosis inhibitors and synthetic and natural product-bas

A short route to heteroarylcarbazoles: Synthesis of new pyrazolylcarbazoles and carbazolylquinolines

A short synthesis of pyrazolylcarbazoles from 9-alkyl-carbazoles in three steps is reported. The acetylcarbazoles prepared by the acetylation of carbazoles with acetic anhydride catalyzed by BiCl3 were converted into chloroaldehydes with Vilsmeier reagent. Condensation of chloroaldehydes with hydrazine followed by cyclization yield the pyrazolylcarbazoles. Carbazolyl chalcones were prepared by the condensation of carbazole-3-aldehyde with o-aminoacetophenone and cyclized to carbazolylquinolone using several catalysts. Cyclization of carbazolyl chalcones with the Vilsmeier reagent yields a mixture of carbazolylquinoline carbaldehydes.

A facile method for the synthesis of acetylcarbazoles and carbazole aldehydes

Acetylation of 9-alkylcarbazoles with acetic anhydride catalyzed by PPh3. HClO4 was reported to give acetylcarbazoles. Carbazole aldehydes were easily synthesized by the Vilsmeier reaction of 9-alkylcarbazoles under microwave condition in good yields.

Studies of the Generation of Excited Singlet Products in the Oxidation of the -CO-CH- Containing Molecules. The Chemiluminescence of Acylcarbazoles

Direct chemiluminescence emissions have been found from the air oxidation of 3-acyl-9-methyl- (1), 3,6-diacyl-9-methyl- (2), and 9-acylcarbazoles (3) due to the generation of an excited singlet state of monocarboxylate ions (from 1 and 2) and the carbazole anion (from 3).The relative intensities vs. the reaction time for the luminescent reaction of 3-isobutyryl-9-methylcarbazole could be interpreted by a reaction scheme involving consecutive reactions.Using this reaction scheme, the values of the decomposition rate of intermediates at 30, 40, and 50 deg C were determined to be 0.19, 0.42, and 0.98 min-1 respectively, which were comparable to the values reported for the decomposition rates of isolated dioxetanes giving excited singlet products.