15109-94-1

Basic information

• Product Name: 2-BROMO-1-(2-FURYL)-1-ETHANONE
• Synonyms: TIMTEC-BB SBB010227;BUTTPARK 147\06-34;2-(2-BROMOACETYL)FURAN;2-BROMO-1-(2-FURYL)-1-ETHANONE;2-BROMO-1-FURAN-2-YL-ETHANONE;2-bromo-1-(2-furyl)ethanone;2-(alpha-Bromoacetyl)furan;2-Bromo-1-(2-furanyl)ethanone
• CAS NO: 15109-94-1
• Molecular Formula: C₆H₅BrO₂
• Molecular Weight: 189.01
• Product Categories: Acetyl Halides;Furans, Benzofurans & Dihydrobenzofurans;Acetyl Halides;Furans, Benzofurans & Dihydrobenzofurans
• Mol File: 15109-94-1.mol
• Article Data: 66

Chemical Properties

• Melting Point: 34 °C
• Boiling Point: 227℃
• Flash Point: 91℃
• Appearance: /
• Density: 1.616
• Vapor Pressure: 0.0815mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 2-BROMO-1-(2-FURYL)-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-(2-FURYL)-1-ETHANONE(15109-94-1)
• EPA Substance Registry System: 2-BROMO-1-(2-FURYL)-1-ETHANONE(15109-94-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 22-34-43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 15109-94-1(Hazardous Substances Data)

Usage

Description

2-BROMO-1-(2-FURYL)-1-ETHANONE is an organic compound with the chemical structure that features a bromine atom attached to a carbonyl group, which is connected to a furyl group. 2-BROMO-1-(2-FURYL)-1-ETHANONE is known for its reactivity and is commonly utilized in the synthesis of various chemical compounds.

Uses

Used in Pharmaceutical Industry:
2-BROMO-1-(2-FURYL)-1-ETHANONE is used as a reagent for the preparation of diaryldihydropyrrolizine derivatives. These derivatives exhibit significant activity as cyclooxygenase and lipoxygenase inhibitors, which are crucial targets for the development of anti-inflammatory and analgesic drugs. The compound's role in this process is to facilitate the formation of these bioactive molecules, contributing to the advancement of pharmaceutical research and drug development.

InChI:InChI=1/C6H5BrO2/c7-4-5(8)6-2-1-3-9-6/h1-3H,4H2

Upstream product

• 186581-53-3 diazomethane 
• 527-69-5 2-furancarbonyl chloride 
• 110-00-9 furan 
• 598-21-0 2-Bromoacetyl bromide 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 62889-08-1 1-(2-furyl)-1-(trimethylsilyloxy)ethylene 
• 614-99-3 Ethyl 2-furoate 
• 74-95-3 1,1-dibromomethane 
• 109988-03-6 2-furyl (trimethylsilyl)methyl ketone 
• 615-08-7 2-furoic anhydride 
• 60-29-7 diethyl ether 
• 18649-64-4 2-ethynylfuran 
• 21443-46-9 2-diazoacetylfuran 

Downstream Products

• 88-14-2 2-furanoic acid 
• 17678-19-2 2-(2-hydroxyacetyl)furan 
• 28795-34-8 2-(furan-2-yl)indolizine 
• 28795-36-0 2-(furan-2-yl)imidazo[1,2-a]pyridine 
• 31877-31-3 ethyl 4-(2-furyl)thiazol-2-carboxylate 
• 64493-95-4 6-furan-2-yl-3-(4-methoxy-phenyl)-[1,2,4]triazine 
• 64541-65-7 6-furan-2-yl-3-phenyl-[1,2,4]triazine 
• 64493-96-5 6-furan-2-yl-3-(3,4,5-trimethoxy-phenyl)-[1,2,4]triazine 
• 21036-72-6 4-furan-2-yl-2-p-tolyl-1⁽³⁾H-imidazole 
• 28989-52-8 2-amino-4-(2-furyl)thiazole 
• 21036-69-1 4-furan-2-yl-2-phenyl-1⁽³⁾H-imidazole 
• 21036-63-5 4-(2-furyl)-2-phenylthiazole 
• 64493-94-3 6-furan-2-yl-3-p-tolyl-[1,2,4]triazine 
• 21036-71-5 2-(4-chloro-phenyl)-4-furan-2-yl-1⁽³⁾H-imidazole 

Relevant articles and documents

Asymmetric synthesis of 7-aza-phomopsolide E and its C-4 epimer

A flexible, enantioselective route to highly functionalized α,β-unsaturated δ-lactones has been applied to the synthesis of 7-aza-phomopsolide E and its C-4 epimer. This approach relies on the application of the Noyori asymmetric hydrogenation of furyl ketone to produce the secondary furyl alcohol in high enantioexcess, which can be stereoselectively transformed into α,β-unsaturated-δ-lactones by a short, highly diastereoselective oxidation and reduction sequence. DCC and acid chloride couplings were used to introduce the side chains of the two natural product analogues.

High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives

A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction

Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.