2,3,4,5,6,7,8,9-octahydro-1H-carbazole

Base Information

• Chemical Name: 2,3,4,5,6,7,8,9-octahydro-1H-carbazole
• CAS No.: 26727-32-2
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• DSSTox Substance ID: DTXSID50497946
• Nikkaji Number: J259.113H
• Mol file: 26727-32-2.mol

Synonyms:2,3,4,5,6,7,8,9-octahydro-1H-carbazole;26727-32-2;octahydrocarbazole;SCHEMBL11593915;DTXSID50497946;2,3,4,5,6,7,8,9-octahydro-1H-carbazol

Chemical Property of 2,3,4,5,6,7,8,9-octahydro-1H-carbazole

Chemical Property:

• Melting Point: 102 °C
• Boiling Point: 165-170 °C(Press: 15 Torr)
• PSA: 15.79000
• Density: 1.085±0.06 g/cm3(Predicted)
• LogP: 2.77230
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 175.136099547
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

2,3,4,5,6,7,8,9-octahydro-1H-Carbazole 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC2=C(C1)C3=C(N2)CCCC3

Technology Process of 2,3,4,5,6,7,8,9-octahydro-1H-carbazole

There total 16 articles about 2,3,4,5,6,7,8,9-octahydro-1H-carbazole 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%

dicyclohexylidenehydrazine (4278-87-9) → 2,3,4,5,6,7,8,9-octahydro-1H-carbazole (26727-32-2)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 4h; Reflux; Inert atmosphere;

DOI:10.1007/s10593-011-0802-4

Reference yield: 92.0%

dodecahydro-1H-carbazole (6326-88-1) → 2,3,4,5,6,7,8,9-octahydro-1H-carbazole (26727-32-2)

Guidance literature:

With chlorohydrido(2,6-bis(di-tert-butylphosphinito)phen-1-yl)iridium(III); sodium t-butanolate; at 172 ℃; for 72h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4cc02073a

Reference yield: 86.0%

dodecahydro-N-ethyl-1H-carbazole (146900-30-3) → 2,3,4,5,6,7,8,9-octahydro-1H-carbazole (26727-32-2) + N-ethyl-1,2,3,4,5,6,7,8-octahydrocarbazole (861622-66-4)

Guidance literature:

With chlorohydrido(2,6-bis(di-tert-butylphosphinito)phen-1-yl)iridium(III); sodium t-butanolate; at 178 ℃; for 48h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4cc02073a

upstream raw materials:

dicyclohexylidenehydrazine

9-chloroacetyl-1,2,3,4,5,6,7,8-octahydro-carbazole

bicyclohexyl-2,2'-dione

9H-carbazole

Downstream raw materials:

1,2,3,4-tetrahydrocarbazole

dodecahydro-1H-carbazole

1,2,3,4,4b,5,6,7,8,8a-decahydro-4aH-carbazole

cis-1,2,3,4,5,6,7,8,8a,9a-decahydrocarbazole

Refernces

• 1、 Brayton, Daniel F.,Jensen, Craig M.. "Solvent free selective dehydrogenation of indolic and carbazolic molecules with an iridium pincer catalyst". . p. 5987 - 5989. Retrieved 2014/05/20.
• 2、 Alekseyev,Kurkin,Yurovskaya. "The Piloty-Robinson reaction of N-substituted piperidin-4-one azines. A novel route for the synthesis of 3,6-diazacarbazole". experimental part. p. 584 - 596. Retrieved 2012/01/12.