149418-41-7

Basic information

• Product Name: 3,4-dibromo-5H-furan-2-one
• Synonyms: 3,4-dibromo-5H-furan-2-one;3,4-Dibromo-2(5H)-furanone ;3,4-Dibromo-2(5H)-furanone 97%
• CAS NO: 149418-41-7
• Molecular Formula: C₄H₂Br₂O₂
• Molecular Weight: 241.88
• Mol File: 149418-41-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 90-94°C
• Boiling Point: 315°C at 760 mmHg
• Flash Point: 144.3°C
• Appearance: /
• Density: 2.566g/cm³
• Vapor Pressure: 0.000449mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 3,4-dibromo-5H-furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dibromo-5H-furan-2-one(149418-41-7)
• EPA Substance Registry System: 3,4-dibromo-5H-furan-2-one(149418-41-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 149418-41-7(Hazardous Substances Data)

Usage

General Description

3,4-dibromo-5H-furan-2-one is a chemical compound with the molecular formula C4H2Br2O2. It is a furan derivative that contains two bromine atoms on the 3 and 4 positions of the furan ring. 3,4-dibromo-5H-furan-2-one is commonly used in the synthesis of various pharmaceuticals and agrochemicals, as well as in organic chemical reactions due to its reactivity and ability to undergo nucleophilic substitution and aromatic substitution reactions. 3,4-dibromo-5H-furan-2-one is also known for its potential antimicrobial and antifungal properties, making it a valuable building block in the development of new drugs and pesticides. However, it is important to handle and use this compound with caution as it is toxic and may have harmful effects on human health and the environment.

InChI:InChI=1/C4H2Br2O2/c5-2-1-8-4(7)3(2)6/h1H2

Upstream product

• 488-11-9 mucobromic acid 
• 766-38-1 mucobromic acid 
• 21285-46-1 Trans-2,3-dibromo-2-butene-1,4-diol 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 
• 28952-71-8 α.β-dibromo-γ-oxy-crotonic acid 
• 32460-04-1 3,4-dibromo-furan-2-carboxylic acid 
• 21577-50-4 mucobromic acid 

Downstream Products

• 329328-49-6 3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one 
• 5635-16-5 3,4-diphenyl-2(5H)-furanone 
• 672304-81-3 3-bromo-4-phenylethynyl-2(5H)-furanone 
• 1402571-22-5 3-bromo-4-(2-methoxy-4-fluorophenyl)furan-2(5H)-one 
• 5400-65-7 2,2'-dimethoxy-4,4'-difluorobiphenyl 
• 4877-93-4 2,2'-Dimethoxybiphenyl 
• 1402571-21-4 3-bromo-4-(2-methoxyphenyl)furan-2(5H)-one 
• 137617-20-0 bromomalonaldehyde dianil bromide 
• 1616889-94-1 3-bromo-4-(5-methyl-2-methoxyphenyl)furan-2(5H)-one 
• 476471-02-0 4-(4-fluorophenyl)-2(5H)-furanone 
• 329328-50-9 3-bromo-4-(4-methoxyphenyl)-2(5H)-furanone 
• 3516-65-2 4-(4-methoxyphenyl)furan-2(5H)-one 

Relevant articles and documents

An efficient and inexpensive multigram synthesis of 3,4-dibromo- and 3,4-dichlorofuran-2(5H)-one

The efficient and inexpensive synthesis of 3,4-dibromo- and 3,4-dichlorofuran-2(5H)-one on a multigram scale by sodium borohydride reduction of mucobromic and mucochloric acid, respectively, is reported. Georg Thieme Verlag Stuttgart.

Synthesis and cytotoxic evaluation of halogenated furanones

Abstract: The objective of the current study is to evaluate the potency of halogen-furan-2(5H)-one-type derivatives against human cancer cell lines. Four known bromofuran-2(5H)-one-type derivatives, as well as five new and two known bromo-4-(phenylamino)furan-2(5H)-one-type compounds and six novel and two known halogen-4-alkyl-5-phenyl-3-(phenylamino)furan-2(5H)-one-type derivatives, were synthesized and evaluated for their anticancer activity against prostate (PC-3) and colon (HCT-116) human cancer cell lines. The results showed that only the bromofuran-2(5H)-ones were cytotoxic in both cell lines. Three of these displayed particularly useful antiproliferative activities, in both cancer cells evaluated. (E)-5-(Bromomethylene)furan-2-(5H)-one was the most active against PC-3 (IC50 0.93 ± 0.02?μM) while 3,4-dibromofuran-2(5H)-one was the most active against HCT-116 (IC50 0.4 ± 0.04?μM). Furthermore, flow cytometry studies revealed that the bromofuran-2(5H)-ones induced cell death by apoptosis. Also, it was found that the cytotoxic furanones induced lipid peroxidation, determined by TBARS assay. Thus, cytotoxicity of the active compounds could be associated with ROS production. Additionally, it must be taken into account that all cytotoxic compounds contain an electrophilic carbon atom in position 4, which can explain, through a non-specific reactivity with nucleophiles, the cytotoxic activity of these compounds. Graphic abstract: [Figure not available: see fulltext.]

Synthesis of rubrolide analogues as new inhibitors of the photosynthetic electron transport chain

Many natural products have been used as a model for the development of new drugs and agrochemicals. Following this strategy 11 rubrolide analogues, bearing electron-withdrawing and -donating groups at both benzene rings, were prepared starting from commercially available mucobromic acid. The ability of all compounds to inhibit the photosynthetic electron transport chain in the chloroplast was investigated. The rubrolide analogues were effective in interfering with the light-driven ferricyanide reduction by isolated chloroplasts. The IC50 values of the most active derivatives are in fact only 1 order of magnitude higher than those of commercial herbicides sharing the same mode of action, such as Diuron (0.27 μM). QSAR studies indicate that the most efficient compounds are those having higher ability to accept electrons, either by a reduction process or by an electrophilic reaction mechanism. The results obtained suggest that the rubrolide analogues represent promising candidates for the development of new active principles targeting photosynthesis to be used as herbicides.