1899-24-7

Usage

Uses

Used in Chemical Synthesis:
5-Bromo-2-furaldehyde is used as a key intermediate in the preparation of isoindolinones from furfural. It is also used in the synthesis of brominated nitrovinylfuran, which exhibits antibacterial activity.
Used in Pharmaceutical Industry:
5-Bromo-2-furaldehyde may be employed for the synthesis of various 5-substituted 2-furaldehydes and anilines through a novel one-pot, two-step amination/Diels-Alder procedure. This allows for the creation of a range of compounds with potential pharmaceutical applications.
Some of the specific syntheses that can be achieved using 5-Bromo-2-furaldehyde include:
5-(5′,8′-dimethyl-9′-tert-butoxycarbonyl-9′H-carbazol-3′-yl)-furan-2-carbaldehyde
5-(6-hydroxyhexyl)-2-furaldehyde
5-methylsulfonyl-2-furaldehyde
5-phenylsulfonyl-2-furaldehyde
5-(4-acetamidobenzylsulfonyl)-2-furaldehyde
5-iodo-2-furaldehyde
These synthesized compounds can be further utilized in the development of new drugs and pharmaceutical agents, showcasing the versatility and importance of 5-Bromo-2-furaldehyde in the field of chemistry and medicine.

InChI:InChI=1/C5H3BrO2/c6-5-2-1-4(3-7)8-5/h1-3H

Upstream product

• 613-75-2 (furan-2-yl)methylene diacetate 
• 7726-95-6 bromine 
• 98-01-1 furfural 
• 107-06-2 1,2-dichloro-ethane 
• 123-31-9 hydroquinone 
• 4915-06-4 5-bromofuran-2-carbonitrile 
• 1137088-24-4 (5-formylfuran-2-yl)(triphenyl-λ5-phosphanyl)gold 
• 35950-55-1 1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene 
• 854753-06-3 bis-(5-hydroxymethyl-[2]furyl)-mercury 
• 854819-96-8 bis-(5-formyl-[2]furyl)-mercury 
• 179055-22-2 N-methyl-N-methoxy-5-bromofuran-2-carboxamide 
• 89167-32-8 5-formyl-[2]furylmercury ⁽¹⁺⁾; chloride 
• 585-70-6 5-bromo-furan-2-carboxylic acid 

Downstream Products

• 18812-29-8 4-Oxo-nonen-(2)-saeure-ethylester 
• 18249-68-8 2-(5'-Brom-2'-furyl)benzimidazol 
• 37128-70-4 2-(5-Brom-2-furyl)-5(6)-nitrobenzimidazol 
• 41260-29-1 3-(5-bromo-furan-2-yl)-2-phenyl-1,2-dihydro-naphtho[2,1-e][1,2,4]triazine 
• 13803-39-9 5-phenylfuran-2-carbaldehyde 
• 3680-96-4 5-morpholinofuran-2-carboxaldehyde 
• 3680-93-1 5-dimethylaminofurfural 
• 61942-48-1 5-<(4-acetamidophenyl)sulphonyl>-2-furancarboxaldehyde 
• 33342-17-5 5-(4'-fluorophenyl)furan-2-carbaldehyde 
• 34070-33-2 5-(4-methoxyphenyl)furan-2-carbaldehyde 
• 52130-30-0 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde 
• 14385-45-6 5-phenylethinyl-2-furancarboxaldehyde 
• 110360-09-3 5-(2-methylphenyl)-2-furancarboxaldehyde 
• 620-02-0 5-Methylfurfural 

Relevant academic research and scientific papers

Synthesis of [2,2’]Bifuranyl-5,5’-dicarboxylic Acid Esters via Reductive Homocoupling of 5-Bromofuran-2-carboxylates Using Alcohols as Reductants?

Herein, we describe an environmentally benign and cost-effective protocol for the synthesis of valuable bifuranyl dicarboxylates, starting with α-bromination of readily accessible furan-2-carboxylates by LiBr and K2S2O8. Furthermore, the bromination intermediate product 5-bromofuran-2-carboxylates were then conducted in a palladium-catalyzed reductive homocoupling reactions in the presence of alcohols to afford bifuranyl dicarboxylates. One of the final products in this protocol, [2,2’]bifuran-5,5’-dicarboxylic acid esters, are essential monomers of poly(ethylene bifuranoate), which can be served as an green and versatile alternative polymer for traditional poly(ethylene terephthalate) that is currently common in technical plastics.

Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity

A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 μg/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile.

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.

Gold-catalysis: Reactions of organogold compounds with electrophiles

Different arylgold(I), one alkynylgold(I), and one vinylgold(I) triphenylphosphane complexes were subjected to electrophilic halogenation reagents. With N-chlorosuccinimid, N-bromosuccinimid, and N-iodosuccinimid as well as the Barluenga reagent, selectively halogenated compounds were obtained. Trifluoroacetic acid, as a source of protons, leads to a clean protodeauration. With N-fluorobenzenesulfonimide or Selectfluor, exclusively a homocoupling was observed. For the precursor of the vinylgold(I) complex, a similar oxidative coupling could be induced by gold(III) chloride. Reactions with silicon or tin electrophiles failed. CSIRO 2010.

Isoquinoline compound melanocortin receptor ligands and methods of using same

The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.

Inhibitors of acyl-coA:cholesterol O-acyltransferase. 2. Identification and structure-activity relationships of a novel series of N-alkyl-N- (heteroaryl-substituted benzyl)-N'-arylureas

A series of N-alkyl-N-(heteroaryl-substituted benzyl)-N'-arylurea and related derivatives represented by 2 and 3 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Among these novel compounds, the type 3 series was superior. A pyrazol-3-yl group on the N-benzyl group of this trisubstituted urea (i.e. 3, Ar1 = pyrazol-3- yl) was identified as a heteroaromatic ring providing a good profile of biological activity. As a result of optimization of the combination with the N-alkyl group (R) and N-aryl group (At3), compound 3aq (FR186054) was identified as a new, orally efficacious ACAT inhibitor, which exhibited potent in vitro ACAT inhibitory activity (rabbit intestinal microsomes IC50 = 99 nM) and excellent hypocholesterolemic effects in cholesterol-fed rats, irrespective of administration mode (ED50 = 0.046 mg/kg dosed via the diet, ED50 = 0.44 mg/kg administered by gavage in PEG400 vehicle). Moreover, a toxicological study revealed compound 3aq to be nontoxic to the adrenal glands of dogs when tested at a single dose of 10 mg/kg po.

Zur Molekueldynamik isomerer antiaromatischer Tetraoxaporphyrinogene(6.0.6.0)-isomere Tetraoxaporphyrin(6.0.6.0)dikationen

Tetraoxaporphyrinogen(2.2.2.2) 1 as well as the tetraoxaporphyrinogens 2 and 3 are highly dynamic molecules by rotation of the trans-ethene and the trans,trans-diene bridges around the ?-bonds, but the tetraoxaporphyrinogen(4.0.4.0) 4 has no dynamic properties.We describe here the synthesis of the tetraoxaporphyrinogen(6.0.6.0) 5.Neither the isomer E,Z,E,E,Z,E-5a nor Z,E,E,Z,E,E-5b are (obviously due to the steric reasons) dynamic molecules.The porphyrinogens 5a as well as 5b are static molecules at any temperatures and as result of their geometry, which is close to planarity, they have clearly antiaromatic, paratropic character.Both isomers can be oxidized to give the corresponding aromatic, diatropic tetraoxaporphyrin(6.0.6.0)dications 16 a and 16b.Quantum mechanical calculations (AM1) are presented.

Syntheses and spectral properties of unsymmetrically 3,5-disubstituted 2,6-dimethyl-1,4-dihydropyridines

Unsymmetrically 3,5-disubstituted 4-(5-X-2-furyl)-2,6-dimethyl-1,4-dihydropyridines (where X = H, Br, NO2) have been synthesized and characterized by spectral methods (IR, UV, 1H NMR and MS). The modified Hantzsch method made it possible to prepare the title compounds as well as their N-alkylated derivatives. The paper also describes the N-alkylation of sodium salts of substituted 1,4-dihydropyridines using the phase-transfer catalysis.

Hypoglycemic 5-substituted oxazolidine-2,4-diones

Hypoglycemic 5-furyl and 5-thienyl derivatives of oxazolidine-2,4-dione and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; and intermediates useful in the preparation of said compounds.