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:

N-{[(4-methylphenyl)sulfonyl]oxy}-1,2,3,9-tetrahydro-4H-carbazol-4-imine

Refernces

• 1、 Ravi Shankar,Vijayakumar,Sivaramakrishnan,Nagarajan. "A catalyst free synthesis of 8, 9, 11-trihalo-5H-benzofuro[3,2-c]carbazol-10-ols". . p. 3979 - 3983. Retrieved 2017.
• 2、 Iida,H. et al.. "-". . p. 766 - 767. Retrieved 1978.
• 3、 Yan, Shaoyu,Wu, Haihong,Wu, Nan,Jiang, Yongwen. "A mild and effective method to synthesize carbazolones by CuI/L-proline-catalyzed intramolecular arylation". . p. 2699 - 2702. Retrieved 2007.
• 4、 Dubois, Eric A.,Van Den Bos, Jan C.,Doornbos, Tamme,Van Doremalen, Peter A. P. M.,Somsen, G. Aernout,Vekemans, Jozef A. J. M.,Janssen, Anton G. M.,Batink, Harry D.,Boer, Gerard J.,Pfaffendorf, Martin,Van Royen, Eric A.,Van Zwieten, Pieter A.. "Synthesis and in vitro and in vivo characteristics of an iodinated analogue of the β-adrenoceptor antagonist carazolol". . p. 3256 - 3262. Retrieved 1996.
• 5、 Clemo,Felton. "-". . p. 700,702. Retrieved 1951.
• 6、 Bhattacherjee, Dhananjay,Ram, Shankar,Chauhan, Arvind Singh,Yamini,Sheetal,Das, Pralay. "Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis". . p. 5934 - 5939. Retrieved 2019/04/08.