64150-61-4

Usage

Uses

Used in Organic Synthesis:
2,3-Dibromobenzofuran is used as a building block in organic synthesis for the creation of various complex organic molecules. Its ability to react with other molecules and form different types of chemical bonds makes it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,3-Dibromobenzofuran is used as a research compound to explore its potential biological and pharmacological activities. Its unique structure and reactivity may contribute to the development of new drugs and therapeutic agents.
However, it is important to handle 2,3-Dibromobenzofuran with caution as it poses certain health and environmental risks due to its toxic and potentially hazardous properties.

Upstream product

• 271-89-6 1-benzofurane 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 54008-77-4 2-bromo-1-benzofuran 

Downstream Products

• 59214-70-9 3-bromobenzofuran 
• 344350-75-0 3-bromo-2-(4-methoxyphenyl)benzo[b]furan 
• 1173273-35-2 C₂₆H₂₀O 
• 271-89-6 1-benzofurane 
• 1224447-51-1 3-bromo-2-(4-chlorophenyl)benzofuran 
• 1224447-48-6 2,3-bis(4-fluorophenyl)benzo[b]furan 
• 1446486-54-9 2,3-di-(m-tolyl)benzofuran 
• 5782-17-2 2,3-bis(4-methoxyphenyl)benzo[b]furan 
• 1579264-22-4 C₂₂H₁₈O₂ 
• 92104-01-3 2-phenyl-3-bromobenzo[b]furan 
• 13054-95-0 2,3-diphenylbenzofuran 
• 1224447-43-1 2,3-bis(4-methylphenyl)benzo[b]furan 

Relevant academic research and scientific papers

Aromatic and Antiaromatic Pathways in Triphyrin(2.1.1) Annelated with Benzo[b]heterocycles

Understanding of the aromatic properties and magnetically induced current densities of highly conjugated chromophores is important when designing molecules with strongly delocalized electronic structure. Linear extension of the triphyrin(2.1.1) skeleton with an annelated benzo[b]heterocycle fragment modifies the aromatic character by extending the electron delocalization pathway. Two-electron reduction leads to an antiaromatic triphyrin(2.1.1) ring and an aromatic benzo[b]heterocycle subunit. Current-density calculations provide detailed information about the observed pathways and their strengths.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

A regio- and chemoselective cross-coupling study using 2,3-dibromobenzofurans and 2,3,5-tribromobenzofuran was achieved with sub-stoichiometric loadings of triarylbismuths as atom-economic reagents under Pd-catalyzed conditions. As part of this study, various 2,3-diaryl- and 2,3,5-triarylbenzofuran products were obtained in high yields, involving one-pot operations and short reaction times.

DIARYLETHENE COMPOUNDS AND USES THEREOF

A compound according to Formula IA and IB, reversibly convertible under photochromic and electrochromic conditions between a ring-open isomer A and a ring-closed isomer B is provided. For substitutent groups, Z is N, O or S; each R1 is independently selected from the group consisting of H, or halo; each R2 is independently selected from the group consisting of H, halo, a polymer backbone, alkyl or aryl; or, when both R2 together form —CH═CH— and form part of a polymer backbone; each R3 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl; each R4 is aryl; and each R5 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl.

Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study

Benzofuroquinolines were prepared by a new type of Pd catalyzed annulation reaction. In the first step, 2-alkynyl-3-bromobenzofurans were prepared by Sonogashira reactions of 2,3-dibromobenzofuran. Their Pd catalyzed reaction with electron-rich anilines afforded benzofuroquinolines by a domino C-N coupling/annulation process. This reaction proceeds as a C,N-cyclization via the nitrogen atom and the ortho-carbon of the aniline. Similarly, furoquinolines were prepared from 2,3-dibromofuran. In contrast, benzofuropyrroles and furopyrroles were formed by N,N-cyclization when electron-poor anilines were used. Earlier, we reported results related to the thiophene and benzothiophene series. Quinolines were formed from 2,3-dibromobenzothiophene when electron rich anilines were used. In contrast, pyrroles were obtained in the case of electron-poor anilines. On the other hand, pyrroles were generally obtained, not depending on the type of aniline, when 2,3-dibromothiophene was employed as the starting material. In the present article, a detailed DFT study related to the mechanism (quinoline versus pyrrole formation) is reported which provides a rationalization of the selectivities observed for the furan, benzofuran, thiophene and benzothiophene series and for the different selectivities observed for electron-rich and -poor anilines.

Synthesis of novel benzo[ b ]furans and benzo[ b ]thiophenes: Analogs of combretastatin and resveratrol

A rapid and efficient synthesis of fused polyphenolic/polymethoxy benzofurans and benzothiophenes that have potential as antitumor agents and components of anti-HIV combination therapy has been achieved.

Efficient synthesis of functionalized dibenzofurans by domino 'twofold Heck/6π-electrocyclization' reactions of 2,3-di- and 2,3,5-tribromobenzofuran

Functionalized dibenzofurans were prepared based on domino 'twofold Heck/6π-electrocyclization' reactions of 2,3-di- and 2,3,5-tribromobenzofuran.

Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease

The invention provides compounds of Formula I: 1where in W is 2These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful to treat diseases or conditions in which α7 is known to be involved.

Substituted 7-aza[2.2.1]bicycloheptanes for the treatment of disease

The invention provides compounds of Formula I: which may be in the form of pharmaceutical acceptable salts or compositions, are useful in treating diseases or conditions in which α7 nicotinic acetylcholine receptors (nAChRs) are known to be involved.

New Class of Chiral Diphosphine Ligands for Highly Efficient Transition Metal-Catalyzed Stereoselective Reactions: The Bis(diphenylphosphino) Five-membered Biheteroaryls

The synthesis and application of three examples of a new class of chiral (C2) atropisomeric diphosphines characterized by two interconnected five-membered heteroaromatic rings, with hindered rotation around the interanular bond, are described.Optically pure (+)- and (-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene (tetraMe-bitianp) (1a) and the parent unsubstituted system (+)- and (-)-bitianp (1b) were synthesized.They were found to be optically stable at 100 deg C and were successfully employed as ligands in the Ru(II)-catalyzed hydrogenation of α- and β-oxo esters to the corresponding α- and β-hydroxy esters and in the hydrogenation of olefinic substrates.The optical and chemical yields were comparable with those reported for the same Ru(II)-binap-catalyzed reactions carried out under the same experimental conditions.The 2,2'-bis(diphenylphosphino)-3,3'-bibenzofuran (1c), the oxygenated analogue of bitianp, was found to be configurationally unstable at room temperature.Complete structural X-ray elucidation of the Pd complexes of 1a-c is reported.The advantages of these biheteroaromatic ligands over the classical biaryl systems are discussed.