2-Phenylbenzofuran

Base Information

• Chemical Name: 2-Phenylbenzofuran
• CAS No.: 1839-72-1
• Molecular Formula: C14H10O
• Molecular Weight: 194.233
• Hs Code.: 2932999099
• European Community (EC) Number: 654-035-7
• DSSTox Substance ID: DTXSID60393243
• Nikkaji Number: J80.328F
• Wikidata: Q82191931
• ChEMBL ID: CHEMBL1643182
• Mol file: 1839-72-1.mol

Synonyms:2-phenylbenzofuran;1839-72-1;2-phenyl-1-benzofuran;2-phenyl-benzofuran;2-phenyl-benzo[b]furan;CHEMBL1643182;C14H10O;Benzofuran, phenyl-;Benzofuran, 2-phenyl-;2-phenyl benzofuran;SCHEMBL731363;DTXSID60393243;BAA83972;BDBM50162941;MFCD00187273;AKOS024323578

Chemical Property of 2-Phenylbenzofuran

Chemical Property:

• Melting Point: 39 °C
• Boiling Point: 347.8 °C
• PSA: 13.14000
• Density: 1.131±0.06 g/cm3(Predicted)
• LogP: 4.09980
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 194.073164938
• Heavy Atom Count: 15
• Complexity: 207

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Phenylbenzofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=CC=CC=C3O2

Technology Process of 2-Phenylbenzofuran

There total 405 articles about 2-Phenylbenzofuran 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: 76.0%

2-bromo-1-benzofuran (54008-77-4) + triphenylbismuthane (603-33-8) → 2-phenylbenzofuran (1839-72-1) + biphenyl (92-52-4,1594-86-1)

Guidance literature:

With palladium diacetate; potassium carbonate; triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 90 ℃; for 1h;

DOI:10.1016/j.tetlet.2012.03.059

Reference yield: 75.0%

triphenylbismuthane (603-33-8) + 2-(β,β-dibromovinyl)phenol (91703-34-3) → 2-phenylbenzofuran (1839-72-1) + biphenyl (92-52-4,1594-86-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 4h; Reagent/catalyst; Concentration; Time; Solvent; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201201314

Reference yield: 64.0%

2-Iodophenol (533-58-4) + phenylacetylene (536-74-3) → 2-phenylbenzofuran (1839-72-1) + 1,4-diphenyl-1,3-butadiyne (886-66-8)

Guidance literature:

With rac-N₂,N₂'-bis(benzyl)-1,1'-binaphthyl-2,2'-diamine; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; In 1,4-dioxane; at 110 ℃; for 55h; Inert atmosphere;

DOI:10.1016/j.tet.2010.01.026

upstream raw materials:

3-Phenylbenzofuran

2-phenoxy-1-phenylethanone

(2-methoxy-phenyl)-phenyl-acetaldehyde

2-(2-hydroxyphenyl)-1-phenylethan-1-one

Downstream raw materials:

3-acetyl-2-phenylbenzofuran

3-(2-phenyl-1-benzofuran)carbaldehyde

2-(2-phenylethyl)phenol

2,3-diphenylbenzofuran

Refernces

• 1、 Kaboudin, Babak,Salemi, Hadi,Mostafalu, Ramin,Kazemi, Foad,Yokomatsu, Tsutomu. "Pd(II)-β-cyclodextrin complex: Synthesis, characterization and efficient nanocatalyst for the selective Suzuki-Miyaura coupling reaction in water". . p. 195 - 199. Retrieved 2016.
• 2、 Rajes, Cheruvallil S.,Givens, Richard S.,Wirz, Jakob. "Kinetics and mechanism of phosphate photorelease from benzoin diethyl phosphate: Evidence for adiabatic fission to an α-keto cation in the triplet state". . p. 611 - 618. Retrieved 2000.
• 3、 Matsuda, Takanori,Abe, Shinya,Ito, Hirotaka,Tsuboi, Tomoya,Kirikae, Haruki,Murakami, Masahiro. "Synthesis of fused and linked benzofurans from 2-alkynylphenol derivatives through rhodium(i)-catalyzed domino-type addition reactions". . p. 888 - 891. Retrieved 2018.
• 4、 Kim, Mijong,Lee, Suyeon,Kim, Kiseong,Shin, Dongwoo,Kim, Hyunwoo,Song, Hyunjoon. "A highly Lewis-acidic Pd(iv) surface on Pd@SiO2 nanocatalysts for hydroalkoxylation reactions". . p. 14938 - 14941. Retrieved 2014.
• 5、 Nakamura, Masaharu,Ilies, Laurean,Otsubo, Saika,Nakamura, Eiichi. "2,3-Disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole". . p. 2803 - 2805. Retrieved 2006.
• 6、 Lips, Sebastian,Frontana-Uribe, Bernardo Antonio,D?rr, Maurice,Schollmeyer, Dieter,Franke, Robert,Waldvogel, Siegfried R.. "Metal- and Reagent-Free Anodic C?C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis". . p. 6057 - 6061. Retrieved 2018.
• 7、 Khan, M. Wahab,Alam, M. Jahangir,Rashid,Chowdhury. "A new structural alternative in benzo[b]furans for antimicrobial activity". . p. 4796 - 4805. Retrieved 2005.
• 8、 Mosleh, Imann,Shahsavari, Hamid R.,Beitle, Robert,Beyzavi, M. Hassan. "Recombinant Peptide Fusion Protein-Templated Palladium Nanoparticles for Suzuki-Miyaura and Stille Coupling Reactions". . p. 2942 - 2946. Retrieved 2020.
• 9、 Kraus, George A.,Zhang, Ning,Verkade, John G.,Nagarajan, Muthukaman,Kisanga, Philip B.. "Deprotonation of benzylic ethers using a hindered phosphazene base. A synthesis of benzofurans from Ortho-substituted benzaldehydes". . p. 2409 - 2410. Retrieved 2000.
• 10、 Chen, Wei,Zhang, Yicheng,Zhang, Lei,Wang, Min,Wang, Lei. "A highly efficient TBAF-promoted intramolecular cyclization of gem-dibromoolefins for the synthesis of 2-bromobenzofurans(thiophenes)". . p. 10476 - 10478. Retrieved 2011.