2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

Base Information

• Chemical Name: 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile
• CAS No.: 100723-77-1
• Molecular Formula: C13H12N2
• Molecular Weight: 196.252
• NSC Number: 54766
• DSSTox Substance ID: DTXSID10288216
• Nikkaji Number: J854.366F
• Wikidata: Q82024535
• Mol file: 100723-77-1.mol

Synonyms:100723-77-1;2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile;6,7,8,9-tetrahydro-5H-carbazole-3-carbonitrile;1H-Carbazole-6-carbonitrile, 2,3,4,9-tetrahydro-;NSC54766;SCHEMBL4032070;DTXSID10288216;CS-B1538;NSC-54766;AKOS023555201;FT-0739028;D77296;EN300-125058;Z1255493270

Chemical Property of 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

Chemical Property:

• Melting Point: 117-119 °C
• Boiling Point: 403.3±40.0 °C(Predicted)
• PKA: 16.46±0.20(Predicted)
• PSA: 39.58000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 2.91838
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 196.100048391
• Heavy Atom Count: 15
• Complexity: 290

Purity/Quality:

98%min ^*data from raw suppliers

2,3,4,9-Tetrahydro-1H-carbazole-6-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=C(C1)C3=C(N2)C=CC(=C3)C#N

Technology Process of 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

There total 12 articles about 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile 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: 91.0%

4-hydrazinobenzonitrile hydrochloride (2863-98-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (100723-77-1)

Guidance literature:

With acetic acid; for 8h; Reflux;

DOI:10.1016/j.tetlet.2018.01.061

Reference yield: 87.0%

4-hydrazinobenzonitrile (17672-27-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (100723-77-1)

Guidance literature:

With acetic acid; for 8.5h; Reflux;

DOI:10.1039/c4ob00635f

Reference yield: 80.0%

1-bromocyclohexane (108-85-0) + 4-cyanophenyldiazonium tetrafluoroborate (2252-32-6) → 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (100723-77-1)

Guidance literature:

1-bromocyclohexane; With chloro-trimethyl-silane; magnesium; ethylene dibromide; lithium chloride; zinc dibromide; In tetrahydrofuran; at 0 - 25 ℃; for 4h; Inert atmosphere;

With zinc dibromide; In tetrahydrofuran; at 25 ℃; for 0.166667h; Inert atmosphere;

4-cyanophenyldiazonium tetrafluoroborate; With chloro-trimethyl-silane; In tetrahydrofuran; at -60 - 125 ℃; regioselective reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1055/s-0030-1258348

upstream raw materials:

4-cyclohexylidenehydrazino-benzonitrile

cyclohexanone

4-amino-3-iodobenzonitrile

4-hydrazinobenzonitrile hydrochloride

Downstream raw materials:

9-(3-(3,5-dimethylphenoxy)propyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

1-(4-cyanophenylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

5,6,7,8-tetrahydro-carbazole-3-carbonimidic acid anilide

9-benzyl-5,6,7,8-tetrahydro-carbazole-3-carbonitrile

Refernces

• 1、 Chen,Lieberman,Larsen,Verhoeven,Reider. "Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones". . p. 2676 - 2677. Retrieved 1997.
• 2、 Przheval'skii, N. M.,Kostromina, L. Yu.,Grandberg, I. I.. "Mechanism of Fischer Reaction. Dependence of Thermal Indolization of Cyclohexanone Arylhydrazones on Nature of Substituent in the Benzene Ring". . p. 154 - 158. Retrieved 1988.
• 3、 Dalvi, Bhakti A.,Lokhande, Pradeep D.. "Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids". . p. 2145 - 2149. Retrieved 2018.
• 4、 Ghumro, Sarfaraz Ali,Saleem, Sana,Al-Rashida, Mariya,Iqbal, Nafees,Alharthy, Rima D.,Ahmed, Shakil,Moin, Syed Tarique,Hameed, Abdul. "N, N -Dimethylpyridin-4-amine (DMAP) based ionic liquids: Evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1 H -tetrazole synthesis". . p. 34197 - 34207. Retrieved 2017.
• 5、 -. "Process for synthesizing [b]-cycloindole derivatives". Paragraph 0039-0041. . Retrieved 2021/04/17.