5-(Bromomethylene)-2(5h)-furanone

Base Information

• Chemical Name: 5-(Bromomethylene)-2(5h)-furanone
• CAS No.: 199744-38-2
• Molecular Formula: C5H3BrO2
• Molecular Weight: 174.982
• European Community (EC) Number: 809-120-5
• ChEMBL ID: CHEMBL4454202
• Nikkaji Number: J1.759.755H,J2.336.506E
• Mol file: 199744-38-2.mol

Synonyms:5-(bromomethylene)-2(5h)-furanone;199744-38-2;(5E)-5-(bromomethylidene)furan-2-one;2(5H)-Furanone, 5-(bromomethylene)-;5-(Bromomethylene)furan-2(5H)-one;starbld0003552;CHEMBL4454202;J-012907;5-(Bromomethylene)-2(5H)-furanone, >=95.0% (HPLC)

Chemical Property of 5-(Bromomethylene)-2(5h)-furanone

Chemical Property:

• Melting Point: 82-86°C
• PSA: 26.30000
• LogP: 1.33570
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 173.93164
• Heavy Atom Count: 8
• Complexity: 169

Purity/Quality:

98% ^*data from raw suppliers

5-(Bromomethylene)-2(5H)-furanone ≥95.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 20240194
• Hazard Codes: 20240194

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)OC1=CBr
• Isomeric SMILES: C\1=CC(=O)O/C1=C/Br
• General Description: 5-(Bromomethylene)-2(5H)-furanone is a synthetic brominated furanone derivative investigated for its potential as a quorum sensing inhibitor, targeting microbial communication and biofilm formation, particularly in *Staphylococcus epidermidis*. Its structure, derived from maleic anhydride, suggests reactivity that may disrupt bacterial signaling pathways, making it a candidate for antimicrobial applications.

Technology Process of 5-(Bromomethylene)-2(5h)-furanone

There total 1 articles about 5-(Bromomethylene)-2(5h)-furanone 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:

3-bromolevulinic acid (62557-43-1) + 5-bromolaevulinic acid (14594-23-1) → 4-bromo-5-(bromomethylene)-2(5H)-furanone (32323-47-0,247167-54-0) + 5-(dibromomethylene)-2(5H)-furanone (32323-44-7) + 5-(bromomethylene)-2(5H)-furanone (199744-38-2)

Guidance literature:

With sulfuric acid;

DOI:10.1016/j.bmc.2010.05.055

Reference yield: 85.0%

5-(bromomethylene)-2(5H)-furanone (199744-38-2) + 4-nitrophenylboronic acid (24067-17-2) → 5-(4-nitrobenzylidene)furan-2(5H)-one (906627-62-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; tetra-(n-butyl)ammonium iodide; cesium fluoride; In water; toluene; for 36h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2011.02.014

Reference yield: 80.0%

5-(bromomethylene)-2(5H)-furanone (199744-38-2) + 4-methoxyphenylboronic acid (5720-07-0) → 5-(4-methoxybenzylidene)furan-2(5H)-one (24962-84-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; tetra-(n-butyl)ammonium iodide; cesium fluoride; In water; toluene; for 36h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2011.02.014

upstream raw materials:

3-bromolevulinic acid

5-bromolaevulinic acid

Downstream raw materials:

5-(4-fluorobenzylidene)furan-2(5H)-one

5-(4-methoxybenzylidene)furan-2(5H)-one

5-(4-nitrobenzylidene)furan-2(5H)-one

5-(4-(trifluoromethyl)benzylidene)furan-2(5H)-one

Refernces

Synthesis of 5-(bromomethylene)furan-2(5H)-ones and 3-(bromomethylene) isobenzofuran-1(3H)-ones as inhibitors of microbial quorum sensing

10.1039/b803926g

This research aimed to synthesize 5-(bromomethylene)furan-2(5H)-ones and 3-(bromomethylene)isobenzofuran-1(3H)-ones, compounds derived from commercially available maleic anhydrides and phthalic anhydrides, with the goal of investigating their potential as inhibitors of microbial quorum sensing (QS), a communication mechanism used by microorganisms to regulate gene expression in response to population density. The study focused on their ability to interfere with microbial communication and biofilm formation by Staphylococcus epidermidis, a bacterium associated with medical implant infections.