2,5-Dimethoxy-Beta-Nitrostyrene is an organic compound belonging to the class of nitrostyrene derivatives. It has significant applications in organic synthesis and medicinal chemistry, often used for synthesizing complex molecules or as an intermediate. Below is a detailed introduction to this compound:
1. Chemical Structure
- Chemical Formula: C10H11NO4
- Molecular Weight: 209.20 g/mol
- Structural Formula:
OCH3 | OCH3-C6H3-CH=CH-NO2Here, methoxy groups (-OCH₃) are located at the 2 and 5 positions, and a nitro group (-NO₂) is attached to the β position.
2. Physical Properties
- Appearance: Typically yellow to orange crystals or powder.
- Melting Point: Approximately 100-105 °C (specific value depends on purity).
- Solubility:
- Soluble in organic solvents (e.g., ethanol, acetone, dichloromethane).
- Insoluble in water.
3. Chemical Properties
- Reactivity of Nitro Group:
- The nitro group (-NO₂) is a strong electron-withdrawing group and can participate in reduction reactions, nucleophilic substitution reactions, etc.
- Reactivity of Double Bond:
- The vinyl group (-CH=CH-) can participate in addition reactions, cyclization reactions, etc.
- Reactivity of Methoxy Group:
- The methoxy group (-OCH₃) is an electron-donating group that can influence the reactivity of the benzene ring.
4. Synthesis Method
2,5-Dimethoxy-Beta-Nitrostyrene can be synthesized through the following steps:
- Starting Material: 2,5-Dimethoxybenzaldehyde.
- Nitroalkene Formation:
- React 2,5-dimethoxybenzaldehyde with nitromethane under basic conditions to form the target product.
- Reaction Equation:
2,5-(OCH3)2-C6H3-CHO + CH3NO2 → 2,5-(OCH3)2-C6H3-CH=CH-NO2
5. Applications
Organic Synthesis
- Intermediate: Used for synthesizing complex organic molecules, such as drugs, natural products, and functional materials.
- Cyclization Reactions: Serves as a precursor in cyclization reactions to generate nitrogen-containing heterocycles.
Medicinal Chemistry
- Drug Intermediate: Used in the synthesis of biologically active molecules, such as anticancer and anti-inflammatory drugs.
- Biological Activity Research: Some nitrostyrene derivatives exhibit potential biological activity and can be used in drug screening.
Materials Science
- Optoelectronic Materials: Nitrostyrene derivatives can be used to prepare optoelectronic functional materials.
6. Safety and Storage
- Safety:
- Avoid direct contact with skin and eyes; wear protective equipment during handling.
- Avoid inhaling dust or vapors; operate in a fume hood.
- Storage:
- Store in a cool, dry place, away from fire sources and oxidizers.
- Keep containers tightly sealed and avoid exposure to light.
Summary
2,5-Dimethoxy-Beta-Nitrostyrene is an important intermediate in organic synthesis, widely used in medicinal chemistry, organic synthesis, and materials science. Its unique chemical structure makes it highly reactive in various reactions. If you have further questions, feel free to ask!
