4-Bromo-2-phenylbenzofuran

Base Information

• Chemical Name: 4-Bromo-2-phenylbenzofuran
• CAS No.: 863870-92-2
• Molecular Formula: C14H9 Br O
• Molecular Weight: 273.129
• DSSTox Substance ID: DTXSID60460989
• Nikkaji Number: J2.223.310F
• Wikidata: Q82285197
• Mol file: 863870-92-2.mol

Synonyms:4-Bromo-2-phenylbenzofuran;863870-92-2;4-bromo-2-phenyl-1-benzofuran;Benzofuran,4-bromo-2-phenyl-;DTXSID60460989;AKOS027380973;CS-16414;CS-0097135;D72205

Chemical Property of 4-Bromo-2-phenylbenzofuran

Chemical Property:

• Vapor Pressure: 1.66E-05mmHg at 25°C
• Refractive Index: 1.652
• Boiling Point: 375.6°C at 760 mmHg
• Flash Point: 181°C
• PSA: 13.14000
• Density: 1.454g/cm³
• LogP: 4.86230
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 271.98368
• Heavy Atom Count: 16
• Complexity: 237

Purity/Quality:

NLT 98% ^*data from raw suppliers

4-BROMO-2-PHENYLBENZOFURAN 95.00% ^*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=C(O2)C=CC=C3Br

Technology Process of 4-Bromo-2-phenylbenzofuran

There total 16 articles about 4-Bromo-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: 97.0%

1,3-dibromo-2-(phenoxymethyl)benzene + benzaldehyde (100-52-7) → 4-bromo-2-phenylbenzo[b]furan (863870-92-2)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 50 ℃; for 2h; Schlenk technique;

DOI:10.1021/acs.orglett.8b01207

Reference yield: 90.0%

3-bromo-2-iodophenol (855836-52-1) + phenylacetylene (536-74-3) → 4-bromo-2-phenylbenzo[b]furan (863870-92-2)

Guidance literature:

With piperidine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; In N,N-dimethyl-formamide; at 60 ℃; for 10h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201304884

Reference yield: 56.0%

O-3-bromophenyl N,N-diethylcarbamate (863870-72-8) + 1-methyl-4-((phenylethynyl)sulfonyl)benzene (28995-88-2) → 4-bromo-2-phenylbenzo[b]furan (863870-92-2)

Guidance literature:

O-3-bromophenyl N,N-diethylcarbamate; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -78 - -65 ℃; for 1.58333h; Inert atmosphere;

1-methyl-4-((phenylethynyl)sulfonyl)benzene; In tetrahydrofuran; cyclohexane; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium hydroxide; In dimethyl sulfoxide; at 140 ℃; for 8h; regioselective reaction;

DOI:10.3390/molecules27020525

upstream raw materials:

3-bromo-2-iodophenol

phenylacetylene

O-3-bromophenyl N,N-diethylcarbamate

O-3-bromo-2-iodophenyl N,N-diethylcarbamate

Downstream raw materials:

2,4-diphenylbenzo[b]furan

4-(3-nitrophenyl)-2-phenylbenzo[b]furan

4-(diphenylhydroxymethyl)-2-phenylbenzo[b]furan

Refernces

• 1、 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.
• 2、 Takeda, Norihiko,Miyata, Okiko,Naito, Takeaki. "Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans". . p. 1491 - 1509. Retrieved 2008/09/19.