766-38-1

Basic information

• Product Name: 3,4-dibromo-5-hydroxyfuran-2(5H)-one
• Synonyms: 3,4-dibromo-5-hydroxyfuran-2(5H)-one;3,4-Dibromo-5-hydroxy-2(5H)-furanone;3,4-Dibromo-5-hydroxy-2,5-dihydrofuran-2-one;2(5H)-Furanone,3,4-dibromo-5-hydroxy-
• CAS NO: 766-38-1
• Molecular Formula: C₄H₂Br₂O₃
• Molecular Weight: 257.86488
• EINECS: 212-164-2
• Mol File: 766-38-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 77 °C
• Boiling Point: 408.9 °C at 760 mmHg
• Flash Point: 201.1 °C
• Appearance: /
• Density: 2.826 g/cm³
• Vapor Pressure: 2.15E-08mmHg at 25°C
• Refractive Index: 1.743
• PKA: 8.29±0.60(Predicted)
• CAS DataBase Reference: 3,4-dibromo-5-hydroxyfuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dibromo-5-hydroxyfuran-2(5H)-one(766-38-1)
• EPA Substance Registry System: 3,4-dibromo-5-hydroxyfuran-2(5H)-one(766-38-1)

Safety Data

• Hazardous Substances Data: 766-38-1(Hazardous Substances Data)

Usage

Description

3,4-dibromo-5-hydroxyfuran-2(5H)-one is an organic compound with the chemical formula C4Br2O3H2 and the CAS number 766-38-1. It is characterized by the presence of two bromine atoms at the 3,4-positions and a hydroxyl group at the 5-position, attached to a furan ring. 3,4-dibromo-5-hydroxyfuran-2(5H)-one has potential applications in various fields due to its unique chemical properties.

Uses

Used in Periodontal Disease Applications:
3,4-dibromo-5-hydroxyfuran-2(5H)-one is used as a periodontal disease marker for disease drug screening. Its presence can indicate the presence of periodontal disease, allowing for targeted treatment and monitoring of the condition.
Used in Anticancer Applications:
3,4-dibromo-5-hydroxyfuran-2(5H)-one is used as an anti-cancer agent, potentially targeting and inhibiting the growth of cancer cells. Its specific mechanism of action and effectiveness in various types of cancer may vary and require further research and clinical trials.
Used in Infectious Disease Applications:
3,4-dibromo-5-hydroxyfuran-2(5H)-one is used as an autoinducer 2 inhibitor and/or therapeutic agent for infectious diseases. By inhibiting the quorum sensing mechanism in bacteria, it can potentially reduce the virulence of pathogens and help in the treatment of various infections.

InChI:InChI=1/C4H2Br2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H

Upstream product

• 124786-35-2 dibromo-malaldehyde 
• 914362-04-2 3,4-dibromo-5-[(2-methoxyethoxy)methoxy]-5H-furan-2-one 
• 98-01-1 furfural 
• 88-14-2 2-furanoic acid 

Downstream Products

• 20030-12-0 3,4-dibromo-5-(2-oxo-2-phenethyl)-5H-furan-2-one 
• 4595-59-9 5-bromopyrimidine 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 85575-99-1 ethyl (2E)-5-bromo-2-penten-4-ynoate 
• 85575-98-0 ethyl (2E,4Z)-4,5-dibromo-2,4-pentadienoate 
• 92576-92-6 4-(3',4'-dimethoxyphenyl)-2,3-dibromocrotonolactone 
• 4499-39-2 4-(4'-methoxyphenyl)-2,3-dibromocrotonolactone 
• 149418-41-7 3,4-dibromo-2(5H)-furanone 
• 21958-21-4 3,4-dibromo-5-(2,4,6-trimethoxy-phenyl)-5H-furan-2-one 
• 21958-20-3 3,4-dibromo-5-(2,3,4-trimethoxy-phenyl)-5H-furan-2-one 
• 27314-17-6 4,5-dibromo-2-(3-trifluoromethyl-phenyl)-2H-pyridazin-3-one 
• 14305-08-9 4,5-dibromo-2-phenylpyridazin-3(2H)-one 
• 21958-19-0 3,4-dibromo-5-(2,4-dimethoxy-phenyl)-5H-furan-2-one 
• 221031-08-9 4,5-dibromo-2-(3,4-difluorophenyl)-2H-pyridazin-3-one 

Relevant articles and documents

Design, synthesis and evaluation of halogenated furanone derivatives as quorum sensing inhibitors in Pseudomonas aeruginosa

The biofilm formation of Pseudomonas aeruginosa (P. aeruginosa) is regulated by a phenomenon of quorum sensing (QS). With 5-hydroxyl-3,4-halogenated-5H-furan-2-ones as beginning, analogs bearing alkyl chains, vinyl bromide, or aromatic rings were designed and synthesized. The minimum inhibitory concentration (MIC) of the compounds against P. aeruginosa was assayed and the biofilm inhibition ratio was determined at different concentrations lower than the MIC. C-5 aromatic substituted furanones showed remarkable biofilm formation as well as inhibition of virulence factor production in P. aeruginosa. Fluorescence report analysis identified the QS regulatory mechanism of the most active compound 29. This study provides us a novel candidate for combating drug resistant bacteria strains by merely inhibiting biofilm formation. Without suppressing the regular life cycle of the bacteria, bacterial resistance mechanisms may not be activated.

Bromofuranone ester compound and preparation method and application thereof

The invention discloses a bromofuranone ester compound and a preparation method and application of the bromofuranone ester compound. The bromofuranone ester compound is applied to preparation of a medicament for treating diabetic foot drug-resistant bacterial infection, and used as an active constituent and pharmaceutically acceptable excipient. The preparation method of the bromofuranone ester compound comprises the following steps: (1) adding a compound I as shown in the formula I to a low-temperature solvent, stirring, dropwise adding bromine slowly, rising the temperature and carrying outa reflux reaction, stopping to react, cooling, performing suction filtration after solids are precipitated, washing a filter cake with a reducing solution and water, and purifying to obtain a compoundII as shown in the formula II; (2) adding the compound II to the solvent, sequentially adding a compound III, a dehydrant and a catalyst, introducing nitrogen, stirring at room temperature and reacting, and carrying out post-processing and purifying to obtain a compound IV as shown in the formula IV.

Design and synthesis of 2(5H)-furanone liquid-crystal compounds based on natural molecules and biphenyl derivatives

Starting from natural molecules, for example l-menthol and amino acids, a series of 2(5H)-furanone liquid-crystal compounds were designed, and synthesized by esterification of N-[5-menthoxy-2(5H)-furanonyl] amino acids with biphenyl-4-ol or biphenyl-4,4′-diol in the presence of dehydrating agents. The structures of all the novel compounds were confirmed by FTIR, 1H NMR, and mass spectroscopy, and by elemental analysis. The liquid-crystal properties of the target compounds were characterized by differential scanning calorimetry (DSC), X-ray diffraction (XRD), and polarization optical microscopy (POM). The DSC and XRD results showed that some compounds containing short alkyl chains or with the phenyl far from the amino in the amino acid unit formed a mesomorphic phase. Products obtained from biphenyl-4,4′-diol were more likely to form a mesomorphic phase. However, POM revealed no optical texture. These investigations provide, for the first time, a basis for application of 2(5H)-furanones in liquid crystals by combination of different functional units, including biphenyl, l-menthol, and amino acids.