6,11-dihydro-5H-benzo[a]carbazole

Base Information

• Chemical Name: 6,11-dihydro-5H-benzo[a]carbazole
• CAS No.: 21064-49-3
• Molecular Formula: C16H13N
• Molecular Weight: 219.286
• NSC Number: 168810
• UNII: 9PA95SS8HV
• DSSTox Substance ID: DTXSID40305026
• Nikkaji Number: J754.465K
• Wikidata: Q82051441
• ChEMBL ID: CHEMBL239937
• Mol file: 21064-49-3.mol

Synonyms:6,11-dihydro-5H-benzo[a]carbazole;21064-49-3;5H-Benzo[a]carbazole, 6,11-dihydro-;NSC-168810;9PA95SS8HV;5H,6H,11H-BENZO[A]CARBAZOLE;6,11-Dihydro-5H-benzo(a)carbazole;5H-Benzo(a)carbazole, 6,11-dihydro-;NSC168810;1,2,7-trihydrobenzo[a]4aH-carbazole;ST076800;Maybridge1_006237;UNII-9PA95SS8HV;Aza-heterocyclic Derivative, 7;CHEMBL239937;SCHEMBL12126575;BDBM19186;HMS559D11;DTXSID40305026;BBL028411;CCG-20433;MFCD00220068;STK874208;AKOS000547063;PD182775;RH 00733;VS-08759;5,11-DIHYDRO-6H-BENZO(A)CARBAZOLE;CS-0313045;EU-0078364;AE-473/30516010;SR-01000493870;SR-01000493870-1;SR-01000493870-2;17-azatetracyclo[8.7.0.0;{2,7}.0;{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaene

Chemical Property of 6,11-dihydro-5H-benzo[a]carbazole

Chemical Property:

• Vapor Pressure: 5.31E-07mmHg at 25°C
• Boiling Point: 423.9oC at 760 mmHg
• Flash Point: 190.6oC
• PSA: 15.79000
• Density: 1.228g/cm3
• LogP: 3.93350
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 219.104799419
• Heavy Atom Count: 17
• Complexity: 287

Purity/Quality:

99%min ^*data from raw suppliers

6,11-dihydro-5H-benzo[a]carbazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C3=CC=CC=C31)NC4=CC=CC=C24

Technology Process of 6,11-dihydro-5H-benzo[a]carbazole

There total 6 articles about 6,11-dihydro-5H-benzo[a]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: 52.0%

phenylhydrazine hydrochloride (59-88-1) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 11H-benzo[a]carbazole (239-01-0) + 5,6-dihydro-11H-benzo[a]carbazole (21064-49-3)

Guidance literature:

With hydrogenchloride; 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate; oxygen; In water; acetonitrile; at 20 ℃; for 24h; Irradiation; Sealed tube;

DOI:10.1021/acs.orglett.9b02939

Reference yield: 29.0%

C16H14BrN (1386384-19-5) → 5,6-dihydro-11H-benzo[a]carbazole (21064-49-3) + C16H15N (4745-77-1)

Guidance literature:

C₁₆H₁₄BrN; With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; triphenylphosphine; In 1,4-dioxane; Reflux;

With sodium tetrahydroborate; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/ol301663h

Reference yield:

phenylhydrazine (100-63-0) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) + methyl iodide (74-88-4) → 6,6a-dihydro-6a-methyl-5H-benzocarbazole (26490-83-5) + 5,6-dihydro-11H-benzo[a]carbazole (21064-49-3)

Guidance literature:

With boron trifluoride diethyl etherate; acetic acid; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF/hexane/HMPA, -78 deg C, 3 h; 2.) 105 deg C, 1.25 h; 3.) reflux, 3 h;

upstream raw materials:

phenylhydrazine

3,4-dihydronaphthalene-1(2H)-one

methyl iodide

C₁₆H₁₄BrN

Downstream raw materials:

(+/-)-trans-6,6a,11,11a-tetrahydro-5H-benzo[a]carbazole

11H-benzo[a]carbazole

Refernces

• 1、 Wu, Ke-Jia,Dai, Li-Xin,You, Shu-Li. "Palladium(0)-catalyzed dearomative arylation of indoles: Convenient access to spiroindolenine derivatives". scheme or table. p. 3772 - 3775. Retrieved 2012/08/29.