Dibenzofuran-2-carbonitrile

Base Information

• Chemical Name: Dibenzofuran-2-carbonitrile
• CAS No.: 20927-96-2
• Molecular Formula: C13H7NO
• Molecular Weight: 193.205
• European Community (EC) Number: 659-357-1
• Nikkaji Number: J3.423.485J
• Mol file: 20927-96-2.mol

Synonyms:dibenzo[b,d]furan-2-carbonitrile;Dibenzofuran-2-carbonitrile;20927-96-2;2-Dibenzofurancarbonitrile;2-CYANODIBENZOFURAN;Oprea1_127017;SCHEMBL16558189;MFCD00092383;AKOS003389120;AS-58889;CS-0060590;W18400;8-oxatricyclo[7.4.0.0?,?]trideca-1(9),2(7),3,5,10,12-hexaene-4-carbonitrile;8-OXATRICYCLO[7.4.0.0(2),?]TRIDECA-1(9),2(7),3,5,10,12-HEXAENE-4-CARBONITRILE

Chemical Property of Dibenzofuran-2-carbonitrile

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 193.052763847
• Heavy Atom Count: 15
• Complexity: 292

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C(O2)C=CC(=C3)C#N

Technology Process of Dibenzofuran-2-carbonitrile

There total 7 articles about Dibenzofuran-2-carbonitrile 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: 60.0%

dibenzofuran (132-64-9,214827-48-2) + bromocyane (506-68-3) → dibenzo[b,d]furan-3-carbonitrile (29021-90-7) + dibenzo[b,d]furan-2-carbonitrile (20927-96-2) + dibenzo-[b,d]furan-4-carbonitrile (51412-72-7) + dibenzo[b,d]furan-1-carbonitrile (141104-58-7)

Guidance literature:

With aluminium trichloride; In carbon disulfide; for 48h; Yields of byproduct given. Title compound not separated from byproducts; Heating;

Reference yield:

2-bromodibenzo[b,d]furan (86-76-0) + 2-methyl-2-phenylmalononitrile (86164-70-7) → dibenzofuran (132-64-9,214827-48-2) + dibenzo[b,d]furan-2-carbonitrile (20927-96-2)

Guidance literature:

With C₁₀H₈Br₂N₂Ni*(x)H₂O; zinc; In N,N-dimethyl acetamide; at 80 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.9b11208

Reference yield:

4-cyanophenol (767-00-0) → 4-phenoxybenzonitrile (3096-81-9) + dibenzo[b,d]furan-2-carbonitrile (20927-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Trimethylacetic acid / 1,2-dichloro-ethane / 12 h / 80 °C

2: caesium carbonate; palladium 10% on activated carbon / N,N-dimethyl acetamide / 16 h / 140 °C

With palladium 10% on activated carbon; caesium carbonate; Trimethylacetic acid; In N,N-dimethyl acetamide; 1,2-dichloro-ethane;

DOI:10.1021/acs.joc.5b00634

upstream raw materials:

dibenzofuran

bromocyane

sodium cyanide

4-cyanophenol

Downstream raw materials:

8-bromodibenzo[b,d]furan-2-carbonitrile