82607-31-6

Usage

Appearance

Yellow crystalline powder

Usage

Organic synthesis and as a reagent in chemical reactions

Chemical structure

Derivative of benzofuran, a heterocyclic compound with a benzene ring fused to a furan ring

Functional groups

Nitro group and methoxy group in the benzofuran ring

Properties

Unique properties and reactivity due to the presence of nitro and methoxy groups

Applications

Pharmaceutical and agrochemical industries as an intermediate in the synthesis of bioactive compounds

Building block

Valuable for synthesizing aromatic and heterocyclic compounds due to its nitro functionality

Upstream product

• 30335-71-8 2-nitro-7-methoxybenzofuran 
• 75-36-5 acetyl chloride 
• 36687-17-9 Nitro-2 methoxy-6 benzofuranne 

Downstream Products

• 109143-20-6 (N,N-dichlorethylamino)-4 methoxy-7 nitro-2 benzofuranne 

Relevant academic research and scientific papers

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

Sur l'orientation et les anomalies de l'acetylation des Bz-methoxy nitro-2 benzofurannes (1)

4-Methoxy-, 5-methoxy- and 7-methoxy-2-nitrobenzofurans have been acetylated via the Friedel-Crafts reaction under the same reaction conditions. 2-Nitrobenzofuran does not undergo acetylation while 6-methoxy-2-nitrobenzofuran only produces decomposition products.As a result of the positive acetylation reactions, 7-acetyl-4-methoxy-, 4-acetyl-5-methoxy- and 4-acetyl-7-methoxy-2-nitrobenzofuran have been prepared.As side products in the acetylation reactions, 4-methoxy-3-(4'-methoxy-2'-nitro-7'-benzofuranyl)-2,3-dihydrobenzofuran-2-one was isolated when 4-methoxy-2-nitrobenzofuran was the starting material and, likewise, when 5-methoxy-2-nitrobenzofuran was the starting material, 3-chloro-5-methoxy-2,3-dihydrobenzofuran-2-one was obtained.Furthermore, 5-methoxy-2-nitrobenzofuran participated in an unexpected chlorination leading to 4-chloro-5-methoxy-2-nitrobenzofuran.