2433-85-4

Basic information

• Product Name: 4,5-Dibromo-2-furaldehyde
• Synonyms: 4,5-DIBROMO-2-FURALDEHYDE;4,5-DIBROMO-FURAN-2-CARBALDEHYDE;VITAS-BB TBB000315;4,5-DIBROMO-2-FURANCARBOXALDEHYDE
• CAS NO: 2433-85-4
• Molecular Formula: C₅H₂Br₂O₂
• Molecular Weight: 253.88
• Product Categories: Furan&Benzofuran
• Mol File: 2433-85-4.mol

Chemical Properties

• Melting Point: 36-37 °C
• Boiling Point: 276.871 °C at 760 mmHg
• Flash Point: 121.248 °C
• Appearance: /
• Density: 2.184 g/cm³
• Vapor Pressure: 0.00468mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4,5-Dibromo-2-furaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dibromo-2-furaldehyde(2433-85-4)
• EPA Substance Registry System: 4,5-Dibromo-2-furaldehyde(2433-85-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2433-85-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4,5-Dibromo-2-furaldehyde is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs. Its reactivity and the presence of bromine atoms make it a valuable building block for the development of new medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 4,5-Dibromo-2-furaldehyde is utilized as a precursor in the production of pesticides and other agrochemicals. Its chemical properties allow it to be a component of compounds that can effectively control pests and diseases in agriculture.
Used in Organic Chemistry as a Reagent:
4,5-Dibromo-2-furaldehyde serves as a reagent in organic chemistry, facilitating various chemical reactions due to its reactive bromine atoms and furan ring. It is particularly useful in the synthesis of heterocyclic compounds, which are important in the creation of complex organic molecules.
Used in Antimicrobial Applications:
4,5-Dibromo-2-furaldehyde is used as an antimicrobial agent for its potential to inhibit the growth of microorganisms. Its bromine content is likely responsible for its biocidal properties, making it a candidate for use in sanitizing products and materials.
Used in Antifungal Applications:
Similarly, 4,5-Dibromo-2-furaldehyde is applied as an antifungal agent, leveraging its ability to prevent the growth of fungi. This property can be harnessed in the development of antifungal medications or treatments for fungal infections.
Used in Anticancer Research:
4,5-Dibromo-2-furaldehyde is being studied for its potential anticancer properties. Its chemical structure may allow it to interact with biological targets in ways that could inhibit cancer cell growth or induce cell death, making it a subject of interest for cancer therapeutics.
While the provided materials do not detail specific industrial applications beyond the general uses mentioned, the above uses are inferred based on the compound's properties and typical applications of similar compounds in various fields.

InChI:InChI=1/C5H2Br2O2/c6-4-1-3(2-8)9-5(4)7/h1-2H

Upstream product

• 98-01-1 furfural 
• 30544-34-4 2,3-dibromofuran 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 18336-86-2 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (4,5-dibromo-furan-2-ylmethylene)-hydrazide 
• 99142-59-3 4-bromo-5-(2,5-dimethylphenyl)furan-2-carbaldehyde 
• 4828-13-1 4,5-dibromo-2-(diethoxymethyl)-furan 
• 99142-60-6 4-bromo-5-(2,4-dimethylphenyl)furan-2-carbaldehyde 
• 93362-27-7 4,5-dibromo-2-furfurylidenecyanoacetate 
• 99142-58-2 4-bromo-5-phenylfuran-2-carbaldehyde 
• 204996-03-2 benzyl 11-(3-bromo-5-formylfuran-2-yl)undec-10-ynoate 
• 57818-37-8 11-(3-methyl-5-pentylfuran-2-yl)undecanoic acid 
• 93362-33-5 2-(4-Bromo-5-phenylsulfanyl-furan-2-ylmethylene)-malononitrile 
• 93362-37-9 2-(5-Benzenesulfonyl-4-bromo-furan-2-ylmethylene)-malononitrile 

Relevant articles and documents

A selective synthesis of 4-bromo-2-furancarboxaldehyde and its pinacolborane derivative

A selective synthesis of ethylene acetal of 4-bromo-2-furancarboxaldehyde (4) and its pinacolborane derivative (5) is described. The synthesis was carried out using 2-furancarboxaldehyde (1) that was brominated to 4,5-dibromo-2- furancarboxaldehyde (2) in an emulsion of aluminum chloride and methylene chloride. The product was isolated, protected as ethylene acetal, and selectively debrominated to the ethylene acetal of 4-bromo-2-furancarboxaldehyde (4) in one step. This moiety was reacted with pinacolborane to give a reactive reagent of Suzuki coupling.

Synthesis of 5-bromo-2-furfural under solvent-free conditions using 1-butyl-3-methylimidazolium tribromide as brominating agent

The development of a facile and general method for the preparation of 5-bromo-2-furfural is described. An excellent yield of high regioselectivity came out of the bromination reaction of 2-furfural with 1-butyl-3- methylimidazolium tribromide under solvent-free conditions.

Synthesis and in vitro protein tyrosine kinase inhibitory activity of furan-2-yl(phenyl)methanone derivatives

A series of novel furan-2-yl(phenyl)methanone derivatives were synthesized, and their structures were established on the basis of 1H-NMR, 13C-NMR and mass spectral data. All the prepared compounds were screened for their in vitro protein tyrosine kinase inhibitory activity and several new derivatives exhibited promising activity, which, in some cases, was identical to, or even better than that of genistein, a positive reference compound. The preliminary structure-activity relationships of these compounds were investigated and are discussed.

Total synthesis of (+)-nakadomarin A

The total synthesis of (+)-nakadomarin A is described. A three-component cycloaddition of a hydroxylamine, aldehyde, and cyclopropane to form a highly functionalized tetrahydro-1,2-oxazine serves as the foundation for this synthesis. The resulting oxazine

4-(2,4-dichloro-5-methoxyphenyl)amino-6-methoxy-7-{[5-substituted -amino)methyl]-3-furyl}-3-quinolinecarbonitriles as kinase inhibitors

This invention relates to compounds having the structure of Formula I wherein R1, R2, R3, and R4 are described herein.

Diastereoselective synthesis of pyrrolidines using a nitrone/cyclopropane cycloaddition: Synthesis of the tetracyclic core of nakadomarin A

(Chemical Equation Presented) The synthesis of the tetracyclic core of nakadomarin A is described. The core contains all the heterocycles and the required stereocenters found in the natural product and provides a promising route to the target itself. The strategy utilizes a general, diastereoselective pyrrolidine synthesis that proceeds via a homo 3 + 2 dipolar cycloaddition. The scope of this methodology is also described.

Halogen Dance Reactions at Thiophenes and Furans: Selective Access to a Variety of New Trisubstituted Derivatives

LDA-induced halogen migrations and their selective preventions on various bromo substituted thiophenes and furans gave upon reaction with electrophiles access to a large variety of new tri-substituted derivatives.Extension of HD-methodology to 5,5'-dibromo-2,2'-bithiophene enabled for the first time control of selective mono- and double halogen migration.