28177-71-1

Usage

Physical State

Pale yellow crystalline solid

Primary Use

Production of pharmaceuticals and pesticides

Medicinal Properties

Used as a precursor in the synthesis of drugs such as paracetamol and atenolol

Other Uses

Building block for the manufacturing of agrochemicals and dyes

Classification

Hazardous material due to its toxic and irritant properties.

Upstream product

• 88-75-5 2-hydroxynitrobenzene 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 5274-70-4 3-nitrosalicylic aldehyde 
• 85-38-1 3-nitrosalicylic acid 

Downstream Products

• 69084-07-7 2-nitro-6-(piperidin-1'-ylmethyl)phenol 
• 85-38-1 3-nitrosalicylic acid 
• 1447608-50-5 tert-butyl 2-[2-(hydroxymethyl)-6-nitrophenoxy]acetate 
• 180148-35-0 (2-methoxy-3-nitro-phenyl)-methanol 

Relevant academic research and scientific papers

Force-Induced Near-Infrared Chromism of Mechanophore-Linked Polymers

A near-infrared (NIR) mechanophore was developed and incorporated into a poly(methyl acrylate) chain to showcase the first force-induced NIR chromism in polymeric materials. This mechanophore, based on benzo[1,3]oxazine (OX) fused with a heptamethine cyanine moiety, exhibited NIR mechanochromism in solution, thin-film, and bulk states. The mechanochemical activity was validated using UV-vis-NIR absorption/fluorescence spectroscopies, gel permeation chromatography (GPC), NMR, and DFT simulations. Our work demonstrates that NIR mechanochromic polymers have considerable potential in mechanical force sensing, damage detection, bioimaging, and biomechanics.

Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human monoamine oxidase inhibitors

A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the positions 5 or 7 with a nitro group. Substitution patterns on both the phenyl ring and the benzofuran moiety determine the affinity for MAO-A or MAO-B. The 2-(3-methoxyphenyl)-5-nitrobenzofuran 9 was the most potent MAO-B inhibitor (IC50 = 0.024 μM) identified in this series, whereas 7-nitro-2-phenylbenzofuran 7 was the most potent MAO-A inhibitor (IC50 = 0.168 μM), both acting as reversible inhibitors. The number and position of the methoxyl groups on the 2-phenyl ring, have an important influence on the inhibitory activity. Molecular docking studies confirmed the experimental results and highlighted the importance of key residues in enzyme inhibition.