27387-31-1

Basic information

• Product Name: 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one
• Synonyms: 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-4-ONE;9-METHYL-1,2,3,9-TETRAHYDRO-CARBAZOL-4-ONE;9-METHYL-1,2,3,9-TETRAHYDRO-4H-CARBAZOL-4-ONE;9-METHYL-1,2,3,4-TETRAHYDRO-4-OXOCARBAZOLE;9-METHYL-1,2.3,4-TETRAHYDRO-4-OXOCARBAZOLE-4-ONE;1,2,3,9-TETRAHYDRO-9-METHYL-4H-CARBAZOL-4-ONE;1,2,3,9-TETRAHYDRO-9-METHYL-4H-CARBAZOLE-4-ONE;1,2,3,9-TETRAHYDRO-9-METHYL CARBAZOLE-4-ONE
• CAS NO: 27387-31-1
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.25
• EINECS: 1308068-626-2
• Product Categories: Aromatics;Heterocycles;Impurities;Intermediates
• Mol File: 27387-31-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 199.0 to 203.0 °C
• Boiling Point: 383.5 °C at 760 mmHg
• Flash Point: 185.7 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 4.39E-06mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 153862
• CAS DataBase Reference: 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one(27387-31-1)
• EPA Substance Registry System: 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one(27387-31-1)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-52/53-25
• Safety Statements: 22-24/25-61-45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 27387-31-1(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is an organic compound with the molecular formula C11H13NO. It is an off-white solid and serves as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting the 5-HT3 receptor.

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is used as a key intermediate in the synthesis of 5-HT3 modulators for the treatment and prevention of 5-HT3 receptor-mediated diseases. These diseases include nausea, vomiting, and migraines, among others. Its role in the development of these medications is crucial due to its ability to modulate the 5-HT3 receptor, which plays a significant role in the aforementioned conditions.
Additionally, 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is recognized as an impurity in Ondansetron (O655000), a widely used antiemetic drug. The presence of this compound in the manufacturing process of Ondansetron highlights its relevance in the pharmaceutical industry, as controlling and monitoring its levels are essential for ensuring the safety and efficacy of the final drug product.

InChI:InChI=1/C13H13NO/c1-14-10-6-3-2-5-9(10)13-11(14)7-4-8-12(13)15/h2-3,5-6H,4,7-8H2,1H3

Upstream product

• 15128-52-6 1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 77-78-1 dimethyl sulfate 
• 6303-88-4 9-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 108367-88-0 9-methyl-1,2,3,9-tetrahydro-carbazol-4-one-phenylhydrazone 
• 7637-07-2 boron trifluoride 
• 64-19-7 acetic acid 
• 124907-00-2 3-[(2-fluorophenyl)amino]cyclohex-2-en-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 348-54-9 2-Fluoroaniline 
• 504-02-9 1,3-cylohexanedione 
• 100-63-0 phenylhydrazine 
• 128266-89-7 cyclohexane-1,3-dione monophenylhydrazone 

Downstream Products

• 38942-83-5 9-methyl-3-morpholin-4-ylmethyl-1,2,3,9-tetrahydro-carbazol-4-one 
• 59943-49-6 dihydro-5,6 methyl-7 pyrimidino<5,4-c>carbazole 
• 173594-86-0 4-chloro-9-methyl-1,9-dihydro-2H-carbazole-3-carboaldehyde 
• 99614-64-9 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 99614-02-5 ondanserton 
• 99614-01-4 Ondansetron hydrochloride 
• 132659-89-3 3-[(dimethylamine)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride 
• 132666-57-0 1-(dimethylamino)methyl-2-methylimidazole 

Relevant articles and documents

Synthesis, crystal structure, computational and photophysical studies of new hydrazono-thiazole derivatives decorated with N-methyl tetrahydrocarbazole pendant

2,3-Dihydro-1H-carbazol-4(9H)-one, obtained from 2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ) oxidation of tetrahydrocarbazole, on methylation with N, N-dimethylformamide dimethyl acetal (DMF-DMA) furnish N-methyl derivative. The thiosemicarbazone of N-methyl derivative on reaction with 2-bromopropionic acid, ethyl bromopyruvate and dimethyl acetylenedicarboxylate (DMAD) afford hydrazono-thiazolidin-4-one derivatives with tetrahydrocarbazole pendant. X-ray diffraction and DFT studies of (Z)-5-methyl-2-((E)-(9-methyl-2,3-dihydro-1H-carbazol-4(9H)-ylidene)hydrazono)thiazolidin-4-one 5 have been reported. The reaction with dimethyl acetylenedicarboxylate (DMAD) and ethyl bromopyruvate take place without any catalyst and organic solvent. The photophysical properties of these compounds were studied by means of UV/visible absorption spectroscopy and fluorescence spectroscopy.

A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i

New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.

Carbodiimide mediated synthesis of some novel 4-thiazolidinones and 2,4-disubstituted thiazoles bearing N-methyl tetrahydrocarbazole moiety

2,3-Dihydro-1H-carbazol-4(9H)-one, obtained from oxidation of tetrahydrocarbazole with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), on reaction with N,N-dimethylformamide dimethyl acetal (DMF-DMA) affords 9-methyl-2,3-dihydro-1H-carbazol-4(9H)-one 3. The thiosemicarbazone derivative 4 of 9-methyl-2,3-dihydro- 1H-carbazol-4(9H)-one on condensation with α-haloacids in presence of dicyclohexyl carbodiimide (DCC) furnish novel thiazolidin-4-ones 5 and on grinding with phenacyl bromides at room temperature produce new thiazole derivatives 6. The structure of all the synthesized compounds has been established by elemental analysis, IR, NMR and mass spectral data. X-Ray crystallographic studies of 2,3-dihydro-1H-carbazol-4(9H)-one 2 have been reported.