2-ethoxy-2-methylbenzo[d][1,3]dioxole
[CAS# 7555-18-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Olefins (cyclic and non-cyclic)
• Name: 2-ethoxy-2-methylbenzo[d][1,3]dioxole
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20
• CAS Registry Number: 7555-18-2
• SMILES: CCOC1(C)Oc2ccccc2O1

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 229.9±29.0 ºC 760 mmHg (Calc.)^*
• Flash point: 74.6±21.6 ºC (Calc.)^*
• Index of refraction: 1.534 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H318
• Precautionary Statements: P280-P305+P351+P338+P310

Discovory and Applicatios

2‑ethoxy‑2‑methylbenzo[d][1,3]dioxole is an organic compound characterized by a benzodioxole core substituted with an ethoxy group and a methyl group at the 2‑position. The benzodioxole moiety consists of a fused benzene and 1,3‑dioxole ring system, which forms a rigid planar structure with potential for π‑stacking interactions and electron delocalization. The introduction of an ethoxy substituent at the 2‑position increases the compound's lipophilicity, while the methyl group adds steric bulk, potentially influencing both reactivity and solubility in organic solvents.

This compound is typically a colorless to pale yellow liquid at room temperature, displaying moderate solubility in common organic solvents such as ethanol, methanol, and chloroform, but limited solubility in water due to the hydrophobic benzodioxole core. Its chemical stability is generally high under ambient conditions, although it may undergo slow oxidation or hydrolysis under strongly acidic or basic conditions.

In terms of chemical reactivity, the electron-rich benzodioxole ring can participate in electrophilic aromatic substitution reactions, particularly at positions ortho and para to the oxygen atoms. The ethoxy group is capable of undergoing typical ether transformations, including cleavage under strong acidic conditions, while the methyl group may be selectively oxidized or halogenated under appropriate conditions. These functional groups make 2‑ethoxy‑2‑methylbenzo[d][1,3]dioxole a useful intermediate in organic synthesis, where it can serve as a building block for more complex heterocyclic compounds or as a precursor for the introduction of additional substituents into the benzodioxole ring.

Due to its structural similarity to naturally occurring benzodioxole derivatives found in essential oils and bioactive plant metabolites, it has potential utility in medicinal chemistry. The compound may be used as a scaffold for designing molecules with potential biological activity, although specific pharmacological effects have not been fully characterized. Its electron-rich ring system can also facilitate coordination with metal ions, suggesting possible applications in materials chemistry and as a ligand in organometallic synthesis.

In synthetic applications, 2‑ethoxy‑2‑methylbenzo[d][1,3]dioxole can be functionalized through standard organic transformations, including halogenation, nitration, and cross-coupling reactions. These modifications allow chemists to access a wide variety of derivatives that can be tailored for specific chemical or physical properties. The compound’s stability and reactivity profile make it suitable for laboratory-scale synthesis as well as potential incorporation into larger chemical manufacturing processes where substituted benzodioxoles are desired.

Overall, 2‑ethoxy‑2‑methylbenzo[d][1,3]dioxole represents a versatile chemical intermediate. Its combination of lipophilic substituents, aromatic heterocyclic structure, and synthetic accessibility provides utility in both research and potential development of bioactive molecules. While specific applications remain to be fully explored, its structural features and functional group compatibility make it a valuable building block in organic synthesis, particularly for chemists working on novel heterocyclic compounds, ligand design, or small-molecule drug discovery.