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

Base Information

• Chemical Name: 9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
• CAS No.: 27387-31-1
• Molecular Formula: C13H13NO
• Molecular Weight: 199.252
• Hs Code.: 2933990090
• UNII: 267IW42T7Z
• DSSTox Substance ID: DTXSID30181811
• Nikkaji Number: J885.804G
• Wikidata: Q27254062
• Mol file: 27387-31-1.mol

Synonyms:27387-31-1;1,2,3,9-TETRAHYDRO-9-METHYL-4H-CARBAZOLE-4-ONE;9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one;9-Methyl-2,3,4,9-tetrahydro-1H-carbazol-4-one;1,2,3,4-Tetrahydro-9-methylcarbazol-4-one;9-methyl-2,3-dihydro-1H-carbazol-4-one;1,2,3,9-TETRAHYDRO-9-METHYL-4H-CARBAZOL-4-ONE;4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-;UNII-267IW42T7Z;267IW42T7Z;MFCD00173748;9-METHYL-2,3-DIHYDRO-1H-CARBAZOL-4(9H)-ONE;Ondansetron hydrochloride dihydrate specified impurity C [EP];9-Methyl-1,2,3,4-tetrahydrocarbazol-4-one;Maybridge1_001957;1,2,3,9-TETRAHYDRO-4-OXO-CARBAZOLE;AMY280;SCHEMBL1146660;HMS547A21;DTXSID30181811;STK723153;AKOS000520398;AB04362;AC-1031;CS-O-31214;CS-W002468;DS-0682;FS-2935;SY030905;EU-0018574;FT-0621676;FT-0642865;FT-0675029;T2942;1,2,3,4-Tetrahydro-9-methyl-4-oxocarbazole;9-methyl-4-oxo-1,2,3,4-tetrahydrocarbazole;EN300-244783;A819041;A851766;SR-01000524011;J-003550;J-503775;SR-01000524011-1;9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one #;Q27254062;Z1201619510;ONDANSETRON HYDROCHLORIDE DIHYDRATE IMPURITY C [EP IMPURITY]

Chemical Property of 9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Chemical Property:

• Vapor Pressure: 4.39E-06mmHg at 25°C
• Melting Point: 199.0 to 203.0 °C
• Refractive Index: 1.647
• Boiling Point: 383.5 °C at 760 mmHg
• Flash Point: 185.7 °C
• PSA: 22.00000
• Density: 1.21 g/cm³
• LogP: 2.69730
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 199.099714038
• Heavy Atom Count: 15
• Complexity: 276

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-52/53-25
• Safety Statements: 22-24/25-61-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C(=O)CCC2)C3=CC=CC=C31
• Uses: 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is used in the preparation of 5-HT3 modulators useful in the treatment and prevention of 5-HT3 receptor-mediated diseases. 1,2,3,4-Tetrahydro-9-methylcarbazol-4-one is an impurity of Ondansetron (O655000).

Technology Process of 9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

There total 24 articles about 9-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-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: 93.0%

1,2,3,9-tetrahydro-4H-carbazol-4-one (15128-52-6) + methyl iodide (74-88-4) → 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one (27387-31-1,808754-65-6)

Guidance literature:

1,2,3,9-tetrahydro-4H-carbazol-4-one; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h;

DOI:10.1071/CH13287

Reference yield: 89.0%

1,2,3,9-tetrahydro-4H-carbazol-4-one (15128-52-6) + dimethyl sulfate (77-78-1) → 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one (27387-31-1,808754-65-6)

Guidance literature:

With sodium hydroxide; at 60 - 70 ℃; for 2h;

DOI:10.1007/BF01665179

Reference yield: 83.0%

9-methyl-2,3,4,9-tetrahydro-1H-carbazole (6303-88-4) → 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one (27387-31-1,808754-65-6)

Guidance literature:

With 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In water; acetonitrile; for 1h;

upstream raw materials:

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

dimethyl sulfate

9-methyl-2,3,4,9-tetrahydro-1H-carbazole

methyl iodide

Downstream raw materials:

4-chloro-9-methyl-1,9-dihydro-2H-carbazole-3-carboaldehyde

ondanserton

1-(dimethylamino)methyl-2-methylimidazole

3-[(dimethylamine)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride

Refernces

• 1、 Romeo, Giuseppe,Materia, Luisa,Pittala, Valeria,Modica, Maria,Salerno, Loredana,Siracusa, Mariangela,Russo, Filippo,Minneman, Kenneth P.. "New 1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives: Analogues of HEAT as ligands for the α1-adrenergic receptor subtypes". . p. 5211 - 5219. Retrieved 2006.
• 2、 Wang, Jie,Wang, Mingyang,Chen, Kehao,Zha, Shanke,Song, Chao,Zhu, Jin. "C-H Activation-Based Traceless Synthesis via Electrophilic Removal of a Directing Group. Rhodium(III)-Catalyzed Entry into Indoles from N-Nitroso and α-Diazo-β-keto Compounds". . p. 1178 - 1181. Retrieved 2016/03/15.