14757-78-9

Usage

Uses

Used in Pharmaceutical Industry:
3-BROMO-2-FORMYLFURAN is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical structure allows it to serve as a building block in the development of new pharmaceutical compounds, contributing to the advancement of drug discovery and innovation.
Used in Chemical Synthesis:
3-BROMO-2-FORMYLFURAN is also used as a key intermediate in the synthesis of various organic compounds, particularly in the field of organic chemistry. Its reactivity and functional groups make it a valuable component in the creation of complex molecules and advanced materials.

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

Upstream product

• 22037-28-1 3-bromofurane 
• 68-12-2 N,N-dimethyl-formamide 
• 38225-32-0 lithium isopropylamide 
• 4885-02-3 Dichloromethyl methyl ether 
• 30544-34-4 2,3-dibromofuran 

Downstream Products

• 14757-79-0 2-formyl-furan-3-carboxylic acid 
• 98-01-1 furfural 
• 181305-77-1 2-(3-Bromo-furan-2-yl)-[1,3]dioxane 
• 817186-42-8 3-phenylethynylfuran-2-carboxaldehyde 
• 99142-63-9 3-phenylfuran-2-carbaldehyde 
• 877176-26-6 3-(4-hydroxyphenyl)-thio-furan-2-carboxaldehyde 
• 188114-19-4 3-(2-Methoxymethoxy-4-methoxy)phenylfuran-2-carboxaldehyde 
• 142016-30-6 3-(p-tolyl)furan-2-carbaldehyde 
• 1254836-23-1 3-(4-fluorophenyl)furan-2-carbaldehyde 

Relevant academic research and scientific papers

π-Bridge Substitution in DASAs: The Subtle Equilibrium between Photochemical Improvements and Thermal Control**

Donor–acceptor Stenhouse adducts (DASAs) are playing an outstanding role as innovative and versatile photoswitches. Until now, all the efforts have been spent on modifying the donor and acceptor moieties to modulate the absorption energy and improve the c

An expedient route to 3-methoxy-2-furaldehyde

An expedient route to 3-methoxy-2-furaldehyde is presented. Georg Thieme Verlag Stuttgart. New York.

AMIDE COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL MICROBICIDE COMPRISING THE COMPOUND AND THE SALT, AND METHOD FOR USING THE AGRICULTURAL AND HORTICULTURAL MICROBICIDE

An amide compound represented by the general formula [I]: or a salt thereof, an agricultural and horticultural microbicide comprising the compound or the salt as an active ingredient, and a method for using the agricultural and horticultural microbicide.

Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives

A range of functionalized heteroaromatic boronic acid derivatives are readily accessed by a diboration/6π-electrocyclization sequence. This study revealed the surprising observation that there is a direct relationship between oxime ether stereochemistry and reactivity towards electrocyclization. Specifically, E-oxime ethers are found to be significantly more reactive than their Z-counterparts (stereochemistry relative to azatriene scaffold). In contrast, the configuration at the azatriene alkene terminus has little impact on reaction rates. Computational analysis offers a rationale for this observation; a Nlone pair→C=C π* orbital interaction lowers the energy of the transition state in the electrocyclization of E-oxime ethers. Finally, unreactive Z-oxime ethers can be converted to the corresponding heterocyclic products by a photolytically promoted E→Z isomerization and electrocyclization sequence.

Practical nonazide synthesis of a D-amino acid oxidase inhibitor via a sequential erlenmeyer-ploechl reaction and ligand-free copper(I) amination protocol

A synthetic route to fused heterocycle 5 (R1 = Et) was developed that avoids the use of troublesome azido functionality. In this approach, 3-bromofuran aldehyde 7 was synthesized from 3-bromofuran 6 using highly regioselective formylation conditions. The crude solution of 7 was treated with hippuric acid under Erlenmeyer-Ploechl conditions to give enamide product 16, which was isolated by crystallization. Intramolecular amination/cyclization to the fused pyrrole was achieved under ligand-free Cu(I) catalysis in toluene, followed by diamine workup to remove the benzoyl protecting group and residual copper. The final product 5 (R1 = Et) was crystallized directly from the reaction mixture, providing up to 60% overall yield over five chemical steps and two isolations.

Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids

Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.

Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS

A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.

Synthesis and SAR studies of novel heteroaryl fused tetracyclic indole-diamide compounds: Potent allosteric inhibitors of the hepatitis C virus NS5B polymerase

Presented here are initial structure-activity relationship (SAR) studies on a series of novel heteroaryl fused tetracyclic indole-based inhibitors of the hepatitis C viral polymerase, NS5B. The introduction of alternative heterocyclic moieties into the indolo-fused inhibitor class significantly expands the reported SAR and resulted in the identification of pyridino analogs, typified by compounds 44 and 45 that displayed excellent potency against the NS5B polymerase of both HCV 1a and HCV 1b genotypes.

5-[3-(4-Benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2, 4-dione and analogues as inhibitors of macrophage elastase

5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2,4-dione and analogues useful as inhibitors of macrophage elastase are disclosed.

Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5- carboxamide, an agonist of the α7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: Synthesis and structure-activity relationship

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide (14, PHA-543,613), a novel agonist of the α7 neuronal nicotinic acetylcholine receptor (α7 nAChR), has been identified as a potential treatment of cognitive deficits in schizophrenia. Compound 14 is a potent and selective a7 nAChR agonist with an excellent in vitro profile. The compound is characterized by rapid brain penetration and high oral bioavailability in rat and demonstrates in vivo efficacy in auditory sensory gating and, in an in vivo model to assess cognitive performance, novel object recognition.