69227-69-6

Usage

Uses

Used in Pharmaceutical Industry:
2,5-dinitrobenzofuran is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the synthesis of drugs with specific therapeutic properties.
Used in Dye Industry:
In the dye industry, 2,5-dinitrobenzofuran is used as a precursor in the synthesis of dyes. Its chemical properties contribute to the development of dyes with desired color characteristics and stability.
Used in Organic Compounds Synthesis:
2,5-dinitrobenzofuran is also used in the synthesis of other organic compounds. Its versatile chemical structure makes it a valuable building block for creating a wide range of organic molecules with various applications.

InChI:InChI=1/C8H4N2O5/c11-9(12)6-1-2-7-5(3-6)4-8(15-7)10(13)14/h1-4H

Upstream product

• 1646-26-0 1-(benzo[b]furan-2-yl)ethanone 
• 104412-87-5 (2S,3S)-2,5-Dinitro-2,3-dihydro-benzofuran-3-ol 
• 69957-38-6 2-(2-Nitroaethyl)-4-nitrophenol 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 14268-23-6 potassium trinitromethanide 
• 97-51-8 5-Nitrosalicylaldehyde 

Relevant academic research and scientific papers

Asymmetric dearomatization of 2-nitrobenzofurans by organocatalyzed one-step Michael addition to access 3,3′-disubstituted oxindoles

An efficient enantioselective dearomatization of 2-nitrobenzofurans was realized via an organocatalyzed one-step Michael addition process. This method provides a facile strategy to access a range of structurally diverse 3,3′-disubstituted oxindoles, which feature an intriguing combination of two privileged motifs including 3-pyrrolyl-substituted-oxindoles and 2,3-dihydrobenzofurans substructures, in excellent results.

Facile synthesis of chiral [2,3]-fused hydrobenzofuran: Via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition

Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.

Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates

The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.

Potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent: Access to 2-nitroarenofurans

The first example of the use of potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent for the construction of a benzofuran moiety mediated by triethylamine has been developed. The method tolerates a variety of functional groups on the starting quaternary ammonium salt and has been successfully extended to polysubstituted benzofurans. Formation of an o-quinone methide intermediate is postulated as a key to the mechanism of this cascade process.

An Improved Synthesis of 2-Nitrobenzofurans

2-Nitrobenzofurans 4 are prepared in improved yields by reacting o-hydroxybenzaldehydes 1 and bromonitromethane (2) at low temperature in order to avoid the dehydration of the aldol intermediate 3 in the alkaline condensation medium.This aldol 3 is then quantitatively dehydrated by heating in acetic anhydride.

Reactions of Salicylaldehydes with Bromonitromethane

Various salicylaldehydes were treated with bromonitromethane in the presence of an inorganic base to give 2-nitrobenzofuran derivatives, and the reaction mechanisms were investigated.The most remarkable feature of the reactions is that 3-hydroxysalicylaldehyde (1k) alone among various hydroxysalicylaldehydes (1b, k, n, r) gave 2-nitro-7-hydroxybenzofuran in good yield.Bromonitromethane reacted with salicylaldehydes at the aldehyde group exclusively to give 1-(2-hydroxyphenyl)-2-bromo-2-nitroethanols (14), followed by cyclization to produce mixtures consisting of cis- and trans-2-nitro-3-hydroxy-2,3-dihydrobenzofurans (8a, b; 9a, b; 10a, b).The stereochemistry of these products is discussed on the basis of the spectral data and chemical reactivities.The intermediates, 2,3-dihydrobenzofurans, underwent dehydration smoothly to give 2-nitrobenzofurans.Keywords - bromonitromethane; salicylaldehyde derivative; ring closure; 2-nitrobenzofuran derivative; cis-2-nitro-3-hydroxy-2,3-dihydrobenzofuran derivative; trans-2-nitro-3-hydroxy-2,3-dihydrobenzofuran derivative; 13C-NMR; stereochemistry; reaction mechanism

Application en serie benzofurannique d'un nouveau procede de nitration par l'acide nitrique en presence de chlorure stannique

A new nitration technique, using nitric acid in the presence of stannic chloride in dichloromethane, has been extended to a series of benzofurans.The ease of performing the reaction as well as the diversity of products that can be obtained under various experimental conditions make it a worthwhile technique.