1899-24-7

Basic information

• Product Name: 5-Bromo-2-furaldehyde
• Synonyms: 5-BROMOFURANCARBOXALDEHYDE;5-BROMOFURFURAL;5-BROMOFURAN-2-CARBOXALDEHYDE;5-BROMO-2-FURALDEHYDE;5-BROMO-2-FURFURAL;5-Bromo-2-furaldehyde, 5-Bromo-2-furfural;5-BROMO-2-FURANALDEHYDE;5-Bromofuraldehyde
• CAS NO: 1899-24-7
• Molecular Formula: C₅H₃BrO₂
• Molecular Weight: 174.98
• EINECS: -0
• Product Categories: Miscellaneous;Aldehydes;Furans, Benzofurans & Dihydrobenzofurans;Furans, Benzofurans & Dihydrobenzofurans;Building Blocks;Furans;FuransHeterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;aldehyde| alkyl bromide
• Mol File: 1899-24-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 82-85 °C(lit.)
• Boiling Point: 112 °C16 mm Hg(lit.)
• Flash Point: 112°C/6mm
• Appearance: Slightly yellow/Powder
• Density: 1.5940 (rough estimate)
• Vapor Pressure: 0.099mmHg at 25°C
• Refractive Index: 1.4450 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• Sensitive: Air Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 108403
• CAS DataBase Reference: 5-Bromo-2-furaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-furaldehyde(1899-24-7)
• EPA Substance Registry System: 5-Bromo-2-furaldehyde(1899-24-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1899-24-7(Hazardous Substances Data)

Usage

Description

5-Bromo-2-furaldehyde is a chemical compound that features a bromo substituent at the 5-position and a formyl group at the 2-position on a furan ring. It is a solid with various applications in chemical synthesis and pharmaceutical industries.

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

Downstream Products

• 3199-50-6 1-(5-bromofuran-2-yl)ethanone 
• 111252-31-4 trans-3-(5-bromofuran-2-yl)propenoic acid 
• 102456-50-8 5-bromo-furfural-palmitoylhydrazone 
• 109188-53-6 5-bromo-furfural-salicyloylhydrazone 
• 6935-76-8 5-bromo-furfural semicarbazone 
• 61833-86-1 3t-(5-bromo-[2]furyl)-1-phenyl-propenone 
• 85460-04-4 (E)-ethyl 3-(5-bromofuran-2-yl)-2-cyanoacrylate 
• 34220-06-9 5-bromo-furfural-phenylhydrazone 
• 84868-62-2 5-bromo-furfural-(2,4-dinitro-phenylhydrazone) 
• 101084-35-9 Methyl-(2-<5-brom-furyl-(2)>-vinyl)-keton 
• 585-70-6 5-bromo-furan-2-carboxylic acid 
• 99834-94-3 1-(5-bromofuran-2-yl)propan-1-one 
• 22868-60-6 5-(piperidin-1-yl)furan-2-carbaldehyde 
• 13803-39-9 5-phenylfuran-2-carbaldehyde 

Relevant articles and documents

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.

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.

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.