5-Bromobenzofuran

Base Information

• Chemical Name: 5-Bromobenzofuran
• CAS No.: 23145-07-5
• Molecular Formula: C8H5 Br O
• Molecular Weight: 197.031
• Hs Code.: 29329990
• European Community (EC) Number: 676-002-6
• DSSTox Substance ID: DTXSID6073441
• Nikkaji Number: J102.252K
• Wikidata: Q72451620
• Mol file: 23145-07-5.mol

Synonyms:5-Bromobenzofuran;5-Bromo-1-benzofuran;23145-07-5;Benzofuran, 5-bromo-;5-bromobenzo[b]furan;5-bromo-benzofuran;MFCD03407317;5-bromobenzo[beta]furan;5-Bromo-1-benzofuran #;5-Bromobenzofuran, 97%;SCHEMBL6733;DTXSID6073441;5-bromobenzo[beta]furan, 98 %;BCP01211;AKOS006230014;AC-6672;AM90076;CS-W003038;CS-W004134;FS-2272;MB02701;SY003919;A4895;B3889;FT-0600516;EN300-114336;W-206816

Chemical Property of 5-Bromobenzofuran

Chemical Property:

• Appearance/Colour: Colorless to pale yellow liquid
• Vapor Pressure: 0.0835mmHg at 25°C
• Melting Point: 8°C(lit.)
• Refractive Index: 1.638
• Boiling Point: 233.8 °C at 760 mmHg
• Flash Point: 95.2 °C
• PSA: 13.14000
• Density: 1.608 g/cm³
• LogP: 3.19530
• Storage Temp.: Refrigerated.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 195.95238
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

5-Bromobenzofuran ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CO2)C=C1Br
• Chemical Composition and Structure: 5-Bromobenzofuran is an organic compound which consists of a benzofuran ring substituted with a bromine atom at the 5-position.
• Uses: Carbonic Anhydrase Inhibitors: ; 5-Bromobenzofuran derivatives have been synthesized and evaluated for their inhibitory activity against cancer-related carbonic anhydrase (CA) isoforms, particularly hCA IX. They have shown promising inhibitory activity against hCA IX and potential as antiproliferative agents against breast cancer cell lines.^[1]; ; Synthetic Intermediates: ; Used as a building block in the synthesis of various organic compounds, including pharmaceutical intermediates. It is primarily used in the chemical industry as a precursor for the synthesis of other organic compounds. It is also employed in the synthesis of specific pharmaceutical intermediates, such as 1-(7-benzofuranyl)-4-methylpiperazine.^[2]
• Analysis Method: Analytical methods for the characterization of 5-Bromobenzofuran and its derivatives may include spectroscopic techniques (e.g., NMR, IR, UV-Vis), chromatography (e.g., HPLC, GC), and elemental analysis for structural and compositional analysis.
• References: [1] Recent Advancements in the Development of Anti-Breast Cancer Synthetic Small Molecules; DOI 10.3390/molecules26247611; [2] A Highly Active Cobalt Catalyst for the General and Selective Hydrogenation of Aromatic Heterocycles; DOI 10.1002/chem.202300561

Technology Process of 5-Bromobenzofuran

There total 21 articles about 5-Bromobenzofuran 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: 88.0%

5-bromo-2,3-dihydrobenzo[b]furan (66826-78-6) → 5-bromobenzofuran (23145-07-5)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In benzene; at 80 ℃;

DOI:10.3987/com-97-7863

Reference yield: 85.0%

1-bromo-4-(2,2-diethoxyethoxy)benzene (112598-18-2) → 5-bromobenzofuran (23145-07-5)

Guidance literature:

With PPA; In benzene; for 4h; Heating / reflux;

Reference yield: 68.0%

4-Bromo-2-(2-nitro-ethyl)-phenol (96853-37-1) → 5-bromobenzofuran (23145-07-5)

Guidance literature:

4-Bromo-2-(2-nitro-ethyl)-phenol; With sodium hydroxide; at 20 ℃; for 0.5h;

With sulfuric acid; at 0 - 20 ℃;

DOI:10.1055/s-2006-926250

upstream raw materials:

chloroacetic acid

5-bromosalicyclaldehyde

1-bromo-4-(2,2-diethoxyethoxy)benzene

5-bromo-2,3-dihydrobenzo[b]furan

Downstream raw materials:

benzo[b]furan-5-carbonitrile

5-(4-pentyl-phenyl)-benzofuran

(5-bromobenzofuran-2-yl)boronic acid

1-(benzofuran-5-yl)propan-2-one

Refernces

• 1、 Jeyaseelan, Rubaishan,Lautens, Mark,Ross, Rachel J.. "Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening". supporting information. . Retrieved 2020/06/29.
• 2、 Shishido, Ryosuke,Sasaki, Ikuo,Seki, Tomohiro,Ishiyama, Tatsuo,Ito, Hajime. "Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C?H Activation with Silyldimesitylborane". supporting information. p. 12924 - 12928. Retrieved 2019/11/05.