20005-42-9

Basic information

• Product Name: 5-(4-Bromophenyl)furfural
• Synonyms: 5-(4-BROMOPHENYL)-2-FURALDEHYDE;5-(4-BROMOPHENYL)-2-FURANCARBALDEHYDE;5-(4-BROMOPHENYL)-2-FURANCARBOXALDEHYDE;5-(4-BROMO-PHENYL)-FURAN-2-CARBALDEHYDE;5-(4-BROMOPHENYL)FURFURAL;AKOS B015971;AKOS BAR-2459;5-P-BROMOPHENYL FURANCARBOXALDEHYDE
• CAS NO: 20005-42-9
• Molecular Formula: C₁₁H₇BrO₂
• Molecular Weight: 251.08
• Mol File: 20005-42-9.mol
• Article Data: 33

Chemical Properties

• Melting Point: 152-155 °C(lit.)
• Boiling Point: 371.9 °C at 760 mmHg
• Flash Point: 178.7 °C
• Appearance: brown powder
• Density: 1.518 g/cm³
• Vapor Pressure: 1E-05mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-(4-Bromophenyl)furfural(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-Bromophenyl)furfural(20005-42-9)
• EPA Substance Registry System: 5-(4-Bromophenyl)furfural(20005-42-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 20005-42-9(Hazardous Substances Data)

Usage

Description

5-(4-Bromophenyl)furfural is an aromatic aldehyde characterized by its brown powder appearance. It has been noted for its potential in chemical reactions, such as the Oxone oxidation process, which can lead to the formation of γ-keto carboxylic acid.

Uses

Used in Chemical Synthesis:
5-(4-Bromophenyl)furfural is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure with a bromine atom attached to a phenyl group and a furan ring makes it a valuable building block in the creation of complex molecules for pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-(4-Bromophenyl)furfural is used as a key component in the development of new drugs. Its ability to be oxidized to γ-keto carboxylic acid can be exploited in the synthesis of novel drug candidates with potential therapeutic applications.
Used in Material Science:
5-(4-Bromophenyl)furfural can be utilized in the field of material science for the development of new materials with specific properties. Its aromatic and bromine-containing structure may contribute to the creation of materials with enhanced stability, reactivity, or other desirable characteristics.
Used in Dye and Pigment Industry:
The brown powder form of 5-(4-Bromophenyl)furfural suggests its potential use in the dye and pigment industry. It could be employed as a colorant or as a starting material for the synthesis of more complex dyes and pigments with specific color properties.
Used in Analytical Chemistry:
Due to its distinct chemical properties, 5-(4-Bromophenyl)furfural may find applications in analytical chemistry as a reagent or a reference compound for the development of new analytical methods or the calibration of existing ones. Its bromine content and furan ring could be particularly useful in this context.

InChI:InChI=1/C11H7BrO2/c12-9-3-1-8(2-4-9)11-6-5-10(7-13)14-11/h1-7H

Upstream product

• 98-01-1 furfural 
• 106-40-1 4-bromo-aniline 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 5467-74-3 4-Bromophenylboronic acid 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 75-61-6 dibromodifluoromethane 
• 857048-92-1 2-(4-bromophenyl)-5-[(prop-2-yn-1-yloxy)methyl]furan 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 589-87-7 1,4-bromoiodobenzene 
• 1276045-68-1 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 106-37-6 1.4-dibromobenzene 
• 32529-50-3 2-(4-bromo-2-furanyl)-1,3-dioxolane 

Downstream Products

• 35274-39-6 5-[5-(4-bromo-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one 
• 41939-41-7 2-(5-(4-bromophenyl)furan-2-yl)-1H-benzo[d]imidazole 
• 41939-47-3 2-[5-(4-bromo-phenyl)-furan-2-yl]-5-nitro-1⁽³⁾H-benzoimidazole 
• 41939-52-0 2-[5-(4-bromo-phenyl)-furan-2-yl]-1-methyl-5-nitro-1H-benzoimidazole 
• 108196-98-1 (Z)-4-<5-(4-bromophenyl)-2-furfurylidene>-2-butenolide 
• 123394-10-5 (E)-4-<5-(4-bromophenyl)-2-furfurylidene>-2-butenolide 
• 139267-94-0 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-p-chlorophenyl-1,2,4-triazole 
• 139267-89-3 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-methyl-1,2,4-triazole 
• 139267-90-6 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-ethyl-1,2,4-triazole 
• 139267-91-7 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-propyl-1,2,4-triazole 
• 139267-92-8 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-phenyl-1,2,4-triazole 
• 62806-35-3 (E)-3-(5-(4-bromophenyl)furan-2-yl)acrylic acid 
• 139267-93-9 4-<5-(4-p-Bromophenyl)-2-furfurylidene>amino-3-mercapto-5-o-hydroxyphenyl-1,2,4-triazole 
• 39170-09-7 5-(4'-bromophenyl)furan-2-carbaldehyde oxime 

Relevant articles and documents

Synthesis of novel diarylpyrrole-2-carbaldehydes by ring transformations

Various diarylpyrrole-2-carbaldehydes were prepared by ring transformation of arylfuran-2-carbaldehydes with anilines in the presence of an acid. The synthesized compounds were characterized through elemental analysis and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).

Synthesis of arylfuran derivatives as potential antibacterial agents

Bacterial infections represent a serious health care problem mainly due to the misuse and overuse of antibiotics, with consequent emergence of multidrug resistant bacterial strains. Then, because the urgent need to find novel and alternative antibacterial agents, the present work focuses on the synthesis of arylfuran derivatives with potential antimicrobial activity. Eighteen arylfuran derivatives were synthesized and evaluated for their antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Among them, seven compounds containing an amino group in their structure showed activity, with compound 24 being the most effective against both Gram-negative (E. coli, MIC = 49 μM) and Gram-positive (S. aureus, MIC = 98 μM) bacteria, besides having exhibited a modest activity against P. aeruginosa (MIC = 770 μM). In addition, based on in silico studies, this is a druglike compound since it does not violate any rules for predicting oral bioavailability. In this context, the significant antibacterial potential and the low similarity with known antibiotics indicate the innovative aspect of compound 24.

Synthesis of novel benzimidazoles and benzothiazoles via furan-2-carboxaldehydes, o-phenylenediamines, and 2-aminothiophenol using Cu(II) Schiff-base@SiO2 as a nanocatalyst

2-(5-Substituted phenyl)furan-2-carboxaldehyde derivatives were prepared by using an efficient copper(II) complex of tetradentate Schiff-base ligand immobilized onto silica as a heterogeneous nanocatalyst [Cu(II) Schiff-base@SiO2] (5.0?mol%) using anilines, sodium nitrite, and furan-2-carboxaldehyde. Furthermore, attractive di-heteroaryl benzo-fused systems such as benzimidazole and benzothiazole derivatives were synthesized using this nanocatalyst (5.0?mol%) via the reaction of o-phenylenediamines and 2-aminothiophenol with 2-(5-substituted phenyl)furan-2-carboxaldehydes in EtOH. The catalyst was characterized by Fourier transform infrared (FT-IR), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDX), X-ray powder diffraction (XRD), and inductively coupled plasma (ICP) techniques. The advantages of the present catalytic system are short reaction times, mild conditions, good to excellent yields, and low amount of nanocatalyst. Moreover, to the best of our knowledge, this is the first time of using the same catalyst in two steps including synthesis of 2-(5-substituted phenyl)furan-2-carboxaldehyde and benzimidazole or benzothiazole derivatives. In addition, the synthesized catalyst was recycled very well and reused several times without significant loss of its catalytic activity.