34070-33-2

Basic information

• Product Name: 5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE
• Synonyms: CHEMBRDG-BB 4003571;ASINEX-REAG BAS 02786279;5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE;5-(4-METHOXYPHENYL)-2-FURALDEHYDE;AKOS BAR-0559;TIMTEC-BB SBB011024;OTAVA-BB 1148436;5-(4-methoxyphenyl)-2-furaldehyde(SALTDATA: FREE)
• CAS NO: 34070-33-2
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• Mol File: 34070-33-2.mol

Chemical Properties

• Melting Point: 42-42.5℃
• Boiling Point: 359.3°C at 760 mmHg
• Flash Point: 171.1°C
• Appearance: /
• Density: 1.167g/cm³
• Vapor Pressure: 2.41E-05mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: Refrigerator
• Solubility: DMSO (Heated), Chloroform, Methanol (Slightly)
• CAS DataBase Reference: 5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE(34070-33-2)
• EPA Substance Registry System: 5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE(34070-33-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 34070-33-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE is used as an intermediate in the synthesis of near-IR fluorescent dyes for various applications, including bioimaging, sensing, and security inks. Its unique chemical structure allows for the creation of dyes with specific properties, such as high photostability and strong absorption in the near-IR region, which is crucial for their performance in different industries.
Used in Bioimaging Applications:
In the field of bioimaging, 5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE is used as a precursor for the development of near-IR fluorescent dyes that can be employed as markers or probes for visualizing biological processes and structures. These dyes are valuable for their ability to penetrate deep into tissues and provide high-contrast images without significant autofluorescence interference.
Used in Sensing Applications:
5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE is also used as a building block for the development of near-IR fluorescent sensors. These sensors can detect specific analytes, such as metal ions or biomolecules, with high sensitivity and selectivity, making them useful in environmental monitoring, medical diagnostics, and chemical analysis.
Used in Security Inks:
In the security industry, 5-(4-METHOXY-PHENYL)-FURAN-2-CARBALDEHYDE is used as a component in the formulation of near-IR fluorescent inks. These inks are applied to documents, currency, and other valuable items to provide a hidden, yet detectable, security feature that can be verified under specific light conditions, deterring counterfeiting and forgery.

InChI:InChI=1/C12H10O3/c1-14-10-4-2-9(3-5-10)12-7-6-11(8-13)15-12/h2-8H,1H3

Upstream product

• 696-62-8 para-iodoanisole 
• 98-01-1 furfural 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 104-94-9 4-methoxy-aniline 
• 27329-70-0 5-formylfurane-2-boronic acid 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 82303-13-7 (4-methoxyphenyl)zinc(II) bromide 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 68-12-2 N,N-dimethyl-formamide 
• 13529-27-6 2-(diethoxymethyl)furan 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 378185-02-5 (5-(diethoxymethyl)furan-2-yl)boronic acid 

Downstream Products

• 41939-39-3 2-(5-(4-methoxyphenyl)furan-2-yl)-1H-benzo[d]imidazole 
• 41939-45-1 2-[5-(4-methoxy-phenyl)-furan-2-yl]-5-nitro-1⁽³⁾H-benzoimidazole 
• 41939-50-8 2-[5-(4-methoxy-phenyl)-furan-2-yl]-1-methyl-5-nitro-1H-benzoimidazole 
• 188437-73-2 (E)-3-[5-(4-Methoxy-phenyl)-furan-2-yl]-acryloyl azide 
• 956296-79-0 ethyl 2-azido-3-[5-(4-methoxyphenyl)-furan-2-yl]acrylate 
• 956296-80-3 2-(4-methoxyphenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester 
• 463351-39-5 5-[5-(4-methoxy-phenyl)-furan-2-ylmethylene]thiazolidine-2,4-dione 
• 329795-36-0 5-[5-(4-methoxy-phenyl)furan-2-ylmethylene]-2-thioxo-dihydrodihydropyrimidine-4,6-dione 
• 39170-17-7 C-(5-(4-methoxyphenyl)furan-2-yl)methylamine 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 34721-80-7 [5-(4-methoxyphenyl)furan-2-yl]methanol 

Relevant articles and documents

New benzimidazolium N-heterocyclic carbene precursors and their related Pd-NHC complex PEPPSI-type: Synthesis, structures, DFT calculations, biological activity, docking study, and catalytic application in the direct arylation

New benzhydryl-5,6-dimethyl-(3-methylbenzyl)benzimidazolium salt as N-heterocyclic carbene precursors and their related new Pd-NHC complex PEPPSI-type with the general formula [PdBr2(NHC)(pyridine)] were prepared and theoretically studied. Quan

Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]

An efficient method for the carbon–carbon bond formation at C-5 position of 2-substituted furans to provide a range of π-diverse 5-aryl-2-substituted furan derivatives in 58–80% yield has been reported. The method employs several advantages such as use of catalytic amount of K3[Fe(CN)6] under mild conditions and short reaction time with high yields. Also, a variety of anilines with a variety of functional groups can be employed for the synthesis of 5-aryl-2-substituted furans. Graphic Abstract: [Figure not available: see fulltext.]

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.

1,3-Dioxane Functionalized Pd-PEPPSI Catalyst for Direct Arylation of Heteroaromatics

A series of benzimidazolium salts (1a-d) and their Pd-PEPPSI complexes (pyridine-enhanced precatalyst preparation, stabilization, and initiation) (2a-d) were prepared to catalyze the direct arylation of heteroaromatics (2-acetylthiophene and 2-furaldehyde) with various aryl bromides. The structures of all isolated compounds were elucidated based on spectroscopic methods (1H and 13C NMR, FT-IR and LC-MS spectroscopy). Under optimized reaction conditions, C5-arylated products were obtained in moderate to excellent yields in the direct arylation of heteroaromatics.

Synthesis of [PdBr2(benzimidazole-2-ylidene)(pyridine)] complexes and their catalytic activity in the direct C[sbnd]H bond activation of 2-substituted heterocycles

A series of unsymmetrical 1,3-disubstituted benzimidazolium chlorides, 2a-f, having two nitrogen atoms substituted by various alkyl groups were synthesized as N-heterocyclic carbene (NHC) precursors in high yields. The benzimidazolium salts are readily co

Synthesis of Quinoxaline-Linked Bis(Benzimidazolium) Salts and Their Catalytic Application in Palladium-Catalyzed Direct Arylation of Heteroarenes

Abstract: In this study, quinoxaline-linked bis(benzimidazolium) salts were synthesized as bis-N-heterocyclic carbene (NHC) precursors. These bis(NHC) precursors were used as multidentate ligands for the construction of bi(hetero)aryls by palladium-cataly

Synthesis, structures, DFT calculations, and catalytic application in the direct arylation of five-membered heteroarenes with aryl bromides of novel palladium-N-heterocyclic carbene PEPPSI-type complexes

A new series of Pd-catalysts based on an N-heterocyclic carbene PEPPSI-type ligand (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation) with the general formula [Pd(ii)Br2(NHC)(pyridine)] was synthesized and fully characterize

Novel Furan-2-yl-1 H-pyrazoles Possess Inhibitory Activity against α-Synuclein Aggregation

A series of novel furan-2-yl-1H-pyrazoles and their chemical precursors were synthesized and evaluated for their effectiveness at disrupting α-synuclein (α-syn) aggregation in vitro. The compounds were found to inhibit α-syn aggregation with efficacy comp

Palladium-carbene catalyzed direct arylation of five-membered heteroaromatics

Due to the industrial importance of bi(hetero)arenes, the synthesis of these compounds by homogeneous Pd-catalyzed direct arylation is an important research topic in modern organic chemistry. In this study, PEPPSI-type, (PEPPSI = Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation), new Pd-catalysts with N-heterocyclic carbene ligand were synthesized, and they were used as catalysts in the synthesis of bi(hetero)arenes by direct arylation process. The structures of Pd-carbene complexes were elucidated by different spectroscopic and analytical techniques such as NMR, FT-IR and elemental analysis. The more detailed structural characterization of one of the complexes was determined by single-crystal X-ray diffraction study. Pd-carbene complexes were used as effective catalysts in the direct arylation of five-membered heteroaromatics such as thiophene, furan and thiazole derivatives with (hetero)aryl bromides for 1 h, in the presence of 1 mol% of catalyst loading, and successful results were obtained.

Discovery of (5-Phenylfuran-2-yl)Methanamine derivatives as new human sirtuin 2 Inhibitors

Human sirtuin 2 (SIRT2), a member of the sirtuin family, has been considered as a promising drug target in cancer, neurodegenerative diseases, type II diabetes, and bacterial infections. Thus, SIRT2 inhibitors have been involved in effective treatment strategies for related diseases. Using previously established fluorescence-based assays for SIRT2 activity tests, the authors screened their in-house database and identified a compound, 4-(5-((3-(quinolin-5-yl)ureido)methyl) furan-2-yl)benzoic acid (20), which displayed 63 ± 5% and 35 ± 3% inhibition against SIRT2 at 100 μM and 10 μM, respectively. The structure-activity relationship (SAR) analyses of a series of synthesized (5-phenylfuran-2-yl)methanamine derivatives led to the identification of a potent compound 25 with an IC50 value of 2.47 μM, which is more potent than AGK2 (IC50 = 17.75 μM). Meanwhile, 25 likely possesses better water solubility (cLogP = 1.63 and cLogS = ?3.63). Finally, the molecular docking analyses indicated that 25 fitted well with the induced hydrophobic pocket of SIRT2.