4-(Fluoren-9-ylidenemethyl)benzonitrile

Base Information

• Chemical Name: 4-(Fluoren-9-ylidenemethyl)benzonitrile
• CAS No.: 27973-41-7
• Molecular Formula: C₂₁H₁₃N
• Molecular Weight: 279.341
• DSSTox Substance ID: DTXSID201266067
• Nikkaji Number: J3.118.929B
• Mol file: 27973-41-7.mol

Synonyms:4-(fluoren-9-ylidenemethyl)benzonitrile;4-(9H-fluoren-9-ylidenemethyl)benzonitrile;SCHEMBL11742789;DTXSID201266067;4-(9H-Fluorene-9-ylidenemethyl)benzonitrile;AA-504/36570059;27973-41-7

Chemical Property of 4-(Fluoren-9-ylidenemethyl)benzonitrile

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 279.104799419
• Heavy Atom Count: 22
• Complexity: 449

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C2=CC4=CC=C(C=C4)C#N

Technology Process of 4-(Fluoren-9-ylidenemethyl)benzonitrile

There total 7 articles about 4-(Fluoren-9-ylidenemethyl)benzonitrile 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: 96.0%

2,2-dibromo-1-(4-cyanophenyl)ethene (131356-52-0) + 5,5-dimethyl-5H-dibenzo[b,d]stannole (5565-85-5) → 4-((9H-fluoren-9-ylidene)methyl)benzonitrile (27973-41-7)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; cesium fluoride; In 1,4-dioxane; at 60 ℃; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1071/CH12060

Reference yield: 88.0%

2-bromo-2'-(bromomethyl)-1,1'-biphenyl (13379-29-8) + N'-(4-cyanobenzylidene)-4-methylbenzenesulfonohydrazide (41780-79-4) → 4-((9H-fluoren-9-ylidene)methyl)benzonitrile (27973-41-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; caesium carbonate; lithium tert-butoxide; In 1,4-dioxane; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b00613

Reference yield: 79.0%

9-(trimethylsilyl)fluorene (7385-10-6) + 4-cyanobenzaldehyde (105-07-7) → 4-((9H-fluoren-9-ylidene)methyl)benzonitrile (27973-41-7) + 4-((9H-fluoren-9-yl)(hydroxy)methyl)benzonitrile

Guidance literature:

With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In dimethyl sulfoxide; at 20 ℃; chemoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1039/d1ob00065a

upstream raw materials:

9-fluorenone

diethyl [(4-cyanophenyl)methyl]phosphonate

9H-fluorene

4-cyanobenzaldehyde

Downstream raw materials:

4-(Bromo-fluoren-9-ylidene-methyl)-benzonitrile