5-Cyano-2-phenyl-benzo[b]furan

Base Information

• Chemical Name: 5-Cyano-2-phenyl-benzo[b]furan
• CAS No.: 79008-77-8
• Molecular Formula: C15H9NO
• Molecular Weight: 219.243
• DSSTox Substance ID: DTXSID30464393
• Nikkaji Number: J1.857.144G
• Mol file: 79008-77-8.mol

Synonyms:5-Cyano-2-phenyl-benzo[b]furan;2-phenylbenzofuran-5-carbonitrile;79008-77-8;SCHEMBL3537582;DTXSID30464393;AJLXGBHFRPBXAJ-UHFFFAOYSA-N

Chemical Property of 5-Cyano-2-phenyl-benzo[b]furan

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 219.068413911
• Heavy Atom Count: 17
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=C(O2)C=CC(=C3)C#N

Technology Process of 5-Cyano-2-phenyl-benzo[b]furan

There total 16 articles about 5-Cyano-2-phenyl-benzo[b]furan 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: 98.0%

2-chloro-4-cyanophenol (2315-81-3) + phenylacetylene (536-74-3) → 2-phenylbenzofuran-5-carbonitrile (79008-77-8)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4cc00815d

Reference yield: 96.0%

2-iodo-4-cyanophenol (2296-23-3) + phenylacetylene (536-74-3) → 2-phenylbenzofuran-5-carbonitrile (79008-77-8)

Guidance literature:

With caesium carbonate; 1,10-Phenanthroline; (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; In toluene; at 110 ℃; for 24h;

DOI:10.1021/ol0272040

Reference yield: 96.0%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + phenylacetylene (536-74-3) → 2-phenylbenzofuran-5-carbonitrile (79008-77-8)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4cc00815d

upstream raw materials:

2-iodo-4-cyanophenol

phenylacetylene

2-bromo-4-cyanophenyl acetate

4-cyanophenol

Downstream raw materials:

5-cyano-2,3-dihydro-2-phenylbenzofuran

Refernces

• 1、 Jayarajan, Ramasamy,Kumar, Rakesh,Gupta, Jagriti,Dev, Gayathri,Kadu, Pradeep,Chatterjee, Debdeep,Bahadur, Dhirendra,Maiti, Debabrata,Maji, Samir K.. "Fabrication of an amyloid fibril-palladium nanocomposite: A sustainable catalyst for C-H activation and the electrooxidation of ethanol". supporting information. p. 4486 - 4493. Retrieved 2019/03/06.
• 2、 Zheng, Hong-Xing,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao. "Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans". . p. 3310 - 3313. Retrieved 2018/06/11.