1,2,3-trimethoxy-5-[(E)-2-nitrovinyl]benzene
[CAS# 6316-70-7]

Identification

• Name: 1,2,3-trimethoxy-5-[(E)-2-nitrovinyl]benzene
• Synonyms: ß-nitro-3,4,5-trimethoxystyrene
• Molecular Formula: C₁₁H₁₃NO₅
• Molecular Weight: 239.22
• CAS Registry Number: 6316-70-7
• SMILES: COC1=CC(=CC(=C1OC)OC)/C=C/[N+](=O)[O-]

Properties

• Density: 1.204 g/cm³, Calc.
• Boiling Point: 374.404 °C (760 mmHg), Calc.
• Flash Point: 166.571 °C, Calc.

Discovery and Applications

1,2,3-Trimethoxy-5-[(E)-2-nitrovinyl]benzene is a compound known for its unique structure and wide applications in organic synthesis and materials science.

The synthesis and characterization of 1,2,3-trimethoxy-5-[(E)-2-nitrovinyl]benzene was described in detail by organic chemistry researchers, focusing on methods to introduce nitrovinyl groups into the benzene ring while maintaining the trimethoxy substituent. Initial studies highlighted its stability and reactivity, which are critical for its subsequent applications.

The benzene nucleus of 1,2,3-trimethoxy-5-[(E)-2-nitrovinyl]benzene is substituted with three methoxy groups at the 1, 2, and 3 positions and has an E-configured nitrovinyl group at the 5 position. This configuration gives it unique optical and electronic properties that are valuable in a variety of chemical transformations.

The compound is a valuable intermediate in organic synthesis, especially in the construction of complex molecules and natural product derivatives. Its nitrovinyl functionality allows for a variety of modifications such as reduction to amino derivatives or coupling reactions for materials science applications.

1,2,3-Trimethoxy-5-[(E)-2-nitrovinyl]benzene is used in materials science for its potential in optoelectronic devices. Research has explored its use in organic light-emitting diodes (OLEDs) and photovoltaic devices due to its electronic properties and its ability to emit light or facilitate charge transfer in electronic applications.

Research efforts continue to explore new synthetic methods and expand the applications of 1,2,3-trimethoxy-5-[(E)-2-nitrovinyl]benzene. Future directions include optimizing its synthesis for industrial-scale production, further elucidating its electronic properties through computational studies, and exploring its other applications in emerging fields such as molecular electronics and biomedicine.

References

2013. Regiospecific Synthesis of Novel Cyclic Nitrostyrenes and 3-Substituted 2-Nitronaphthalenes. Synthesis, 45(14).
DOI: 10.1055/s-0033-1338867

2020. Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes. Synthesis, 52(22).
DOI: 10.1055/s-0040-1707396

2021. Perspectives on SARS-CoV-2 Main Protease Inhibitors. Journal of Medicinal Chemistry, 64(22).
DOI: 10.1021/acs.jmedchem.1c00409