9-Benzylidene-4-azafluorene

Base Information

• Chemical Name: 9-Benzylidene-4-azafluorene
• CAS No.: 67294-75-1
• Molecular Formula: C19H13N
• Molecular Weight: 255.319
• DSSTox Substance ID: DTXSID60385224
• Mol file: 67294-75-1.mol

Synonyms:9-benzylidene-4-azafluorene;Oprea1_654503;67294-75-1;DTXSID60385224

Chemical Property of 9-Benzylidene-4-azafluorene

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 255.104799419
• Heavy Atom Count: 20
• Complexity: 366

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C2C3=C(C4=CC=CC=C42)N=CC=C3

Technology Process of 9-Benzylidene-4-azafluorene

There total 6 articles about 9-Benzylidene-4-azafluorene 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:

3-iodopyridine (1120-90-7) + diphenyl acetylene (501-65-5) → (Z)-5-benzylidene-5H-indeno[1,2-b]pyridine (67294-75-1) + (E)-5-benzylidene-5H-indeno[1,2-b]pyridine (67294-76-2) + (Z)-9-benzylidene-2-aza-9H-fluorene + (E)-9-benzylidene-2-aza-9H-fluorene

Guidance literature:

With tetrabutyl-ammonium chloride; sodium acetate; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 48h;

DOI:10.1021/ol000220h

Reference yield:

2-phenyl-3-(2-phenylethynyl)pyridine (1398509-70-0) → (Z)-5-benzylidene-5H-indeno[1,2-b]pyridine (67294-75-1) + (E)-5-benzylidene-5H-indeno[1,2-b]pyridine (67294-76-2)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; at 120 ℃; for 8h; Overall yield = 71 %; Inert atmosphere;

DOI:10.1021/ol302375c

Reference yield:

2-chloro-3-(2-phenylethynyl)pyridine (111079-39-1) → (Z)-5-benzylidene-5H-indeno[1,2-b]pyridine (67294-75-1) + (E)-5-benzylidene-5H-indeno[1,2-b]pyridine (67294-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd catalyst; alkaline condition / Heating; Inert atmosphere

2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / 120 °C / Inert atmosphere

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; 1: |Suzuki Coupling;

DOI:10.1021/ol302375c

upstream raw materials:

3-iodopyridine

diphenyl acetylene

2-chloro-3-(2-phenylethynyl)pyridine

phenylacetylene

Refernces

• 1、 Larock,Tian. "Synthesis of 9-alkylidene-9H-fluorenes by a novel, palladium-catalyzed cascade reaction of aryl halides and 1-aryl-1-alkynes". . p. 7372 - 7379. Retrieved 2007/10/03.
• 2、 Varlamov, A. V.,Levov, A. N.,Aliev, A. E.,Vener, M. V.,Ustenko, A. A.,Prostakov, N. S.. "SYNTHESIS, CONFIGURATION, AND TRANSFORMATIONS OF 9-(N-ARYLMETHYLENEAMINOMETHYLENE)-4-AZAFLUORENES". . p. 314 - 319. Retrieved 2007/10/02.