2,3-dihydro-1H-carbazol-4(9H)-one

Base Information

• Chemical Name: 2,3-dihydro-1H-carbazol-4(9H)-one
• CAS No.: 15128-52-6
• Molecular Formula: C12H11NO
• Molecular Weight: 185.225
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID801290622
• Nikkaji Number: J1.202.338C,J291.446H
• Mol file: 15128-52-6.mol

Synonyms:1,2,3,9-tetrahydro-4H-carbazol-4-one

Chemical Property of 2,3-dihydro-1H-carbazol-4(9H)-one

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 3.59E-06mmHg at 25°C
• Melting Point: 224-226 ºC
• Refractive Index: 1.689
• Boiling Point: 386.3 ºC at 760 mmHg
• PKA: 15.84±0.20(Predicted)
• Flash Point: 194.5 ºC
• PSA: 32.86000
• Density: 1.275 g/cm³
• LogP: 2.68690
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 185.084063974
• Heavy Atom Count: 14
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,9-Tetrahydro-4H-carbazol-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C(=O)C1)C3=CC=CC=C3N2
• Uses: A carbazole derivative with antimycobacterial activity.

Technology Process of 2,3-dihydro-1H-carbazol-4(9H)-one

There total 61 articles about 2,3-dihydro-1H-carbazol-4(9H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

3-[(2-iodophenyl)amino]cyclohex-2-en-1-one (85239-68-5) → 1,2,3,9-tetrahydro-4H-carbazol-4-one (15128-52-6)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium acetate; tris-(o-tolyl)phosphine; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 0.5h; Irradiation;

DOI:10.1002/hlca.200490020

Reference yield: 92.0%

methyl 6-(2-nitrophenyl)-5-oxohexanoate (1172640-24-2) → 1,2,3,9-tetrahydro-4H-carbazol-4-one (15128-52-6)

Guidance literature:

With hydrogenchloride; iron; In water; at 110 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1002/jhet.22

Reference yield: 91.0%

1,2,3,4-tetrahydrocarbazole (942-01-8) → 1,2,3,9-tetrahydro-4H-carbazol-4-one (15128-52-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; water; at 0 ℃;

DOI:10.1055/s-2004-834831

upstream raw materials:

1,2,3,4-tetrahydrocarbazole

cyclohexane-1,3-dione monophenylhydrazone

3-(2-bromoanilino)-cyclohex-2-en-1-one

3-[(2-iodophenyl)amino]cyclohex-2-en-1-one

Downstream raw materials:

9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

9H-carbazol-4-ol

cis-2,3,4,4a,9,9a-hexahydro-1H-carbazole

3-morpholin-4-ylmethyl-1,2,3,9-tetrahydro-carbazol-4-one

Refernces

Expedient and green synthesis of some novel 4-thiazolidinones and new 2,4-disubstituted thiazoles with tetrahydro carbazole pendant

10.2174/157017812803521081

The research focuses on the expedited and green synthesis of novel 4-thiazolidinones and new 2,4-disubstituted thiazoles with a tetrahydro carbazole pendant. The purpose of this study is to develop an efficient and environmentally friendly method for synthesizing these heterocyclic compounds, which are known for their biological activities and potential applications in pharmaceuticals and optoelectronic devices. The researchers utilized N-methylpyridinium tosylate, an ionic liquid, as a catalyst for the cyclocondensation reaction of 2-(2,3-dihydro1H-carbazol-4(9H)-ylidene)hydrazinecarbothioamide with α-haloacids, achieving quantitative yields in a short time. They also reported a solvent-free grinding method for the synthesis of 2,4-disubstituted thiazoles. The chemicals used in the process include 2,3-dihydro-1H-carbazol-4(9H)-one, thiosemicarbazide, chloroacetic acid, 2-bromopropionic acid, and substituted phenacyl bromides. The study concludes that the use of the ionic liquid not only simplifies the work-up process but also results in faster reactions and higher yields compared to conventional methods, with the added benefit of being recoverable and reusable for multiple reaction cycles without affecting product yield.