1,2,3,4-Tetrahydrocarbazole

Base Information

• Chemical Name: 1,2,3,4-Tetrahydrocarbazole
• CAS No.: 942-01-8
• Molecular Formula: C12H13 N
• Molecular Weight: 171.242
• Hs Code.: 29339900
• European Community (EC) Number: 213-385-7
• NSC Number: 17329
• UNII: 8ZLK0TSX93
• DSSTox Substance ID: DTXSID00240969
• Nikkaji Number: J48.446F,J3.171.756F
• Wikidata: Q27271250
• ChEMBL ID: CHEMBL1911317
• Mol file: 942-01-8.mol

Synonyms:1,2,3,4-tetrahydrocarbazole;1234-THC

Chemical Property of 1,2,3,4-Tetrahydrocarbazole

Chemical Property:

• Appearance/Colour: beige powder.
• Vapor Pressure: 0.000437mmHg at 25°C
• Melting Point: 118-120 ºC
• Refractive Index: 1.6544 (estimate)
• Boiling Point: 325-330 ºC
• PKA: 17.84±0.20(Predicted)
• Flash Point: 142.1 °C
• PSA: 15.79000
• Density: 1.151 g/cm³
• LogP: 3.04670
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water. Solubility in methanol (almost transparency).
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 171.104799419
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1CCC2=C(C1)C3=CC=CC=C3N2
• Uses: It finds its application as a pharmaceutical intermediate and in the synthesis of aspidospermidine alkaloids. 1,2,3,4-Tetrahydrocarbazole can be used as a starting material to prepare: Spiro[cyclopentane-1,2′-indolin-3′-one] by photooxygenation. 9-Acyl-1,2,3,4-tetrahydrocarbazoles by N-acylation reactions. Carbazole via palladium-catalyzed asymmetric hydrogenation reaction.

Technology Process of 1,2,3,4-Tetrahydrocarbazole

There total 195 articles about 1,2,3,4-Tetrahydrocarbazole 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: 99.0%

phenylhydrazine hydrochloride (59-88-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1,2,3,4-tetrahydrocarbazole (942-01-8)

Guidance literature:

With acetic acid; at 90 - 120 ℃; for 1h; Temperature;

Reference yield: 99.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + phenylhydrazine (100-63-0) → 1,2,3,4-tetrahydrocarbazole (942-01-8)

Guidance literature:

With potassium hydrogensulfate; silica gel; for 0.0138333h; microwave irradiation;

DOI:10.1080/00397910600764766

Reference yield: 96.0%

2′-nitro-4,5-dihydro-[1,1′-biphenyl]-2(3H)-one (176042-31-2) → 1,2,3,4-tetrahydrocarbazole (942-01-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 2h; under 760 Torr;

DOI:10.1016/j.tet.2006.11.052

upstream raw materials:

1-(1,2,3,4-tetrahydro-carbazol-9-yl)-cyclopentanecarboxylic acid

cyclohexanone

acetic acid

phenylhydrazine

Downstream raw materials:

9-(toluene-4-sulphonyl)-2,3,4,9-tetrahydro-1H-carbazole

9H-carbazole

(+/-)-trans-1,2,3,4,4a,9a-hexahydro-carbazole

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

Refernces

• 1、 Ghobadian, Roshanak,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Edraki, Najmeh,Akbarzadeh, Tahmineh,Sharifzadeh, Mohammad,Bukhari, Syed Nasir Abbas,Amini, Mohsen. "Novel tetrahydrocarbazole benzyl pyridine hybrids as potent and selective butryl cholinesterase inhibitors with neuroprotective and β-secretase inhibition activities". . p. 49 - 60. Retrieved 2018.
• 2、 Marshalkin,Yakhontov. "-". . . Retrieved 1972.
• 3、 Zhong, Liang,Chuah, Gaik-Khuan. "Fischer indole synthesis over hydrous zirconia-supported niobium oxide". . p. 1027 - 1033. Retrieved 2009.
• 4、 Teuber et al.. "-". . p. 3089. Retrieved 1978.
• 5、 Charvieux, Aubin,Hammoud, Abdul Aziz,Duclos, Marie-Christine,Duguet, Nicolas,Métay, Estelle. "Synthesis of indoles through acceptorless dehydrogenative coupling catalyzed by nickel on silica-alumina". supporting information. . Retrieved 2021/07/25.
• 6、 Qiu, Yichen,Puni, Kararaina Te,Duplan, Clotilde C.,Lindsay, Ashley C.,Sperry, Jonathan. "Tetrahydrocarbazoles by mechanochemical Fischer indolisation". supporting information. . Retrieved 2021/05/26.