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Dimethylbenzofuran

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Identification
Molecular formula
C10H10O
CAS number
89-70-1
IUPAC name
2,4-dimethylbenzofuran;3,6-dimethylbenzofuran;4,7-dimethylbenzofuran;5,6-dimethylbenzofuran
State
State

At room temperature, dimethylbenzofuran is a liquid. It may crystallize upon cooling, depending on the specific isomer content.

Melting point (Celsius)
8.00
Melting point (Kelvin)
281.20
Boiling point (Celsius)
242.10
Boiling point (Kelvin)
515.20
General information
Molecular weight
146.19g/mol
Molar mass
146.1880g/mol
Density
1.0763g/cm3
Appearence

Dimethylbenzofuran is typically a colorless to pale yellow liquid. It may appear crystalline when solidified. Being a derivative of benzofuran, it retains an aromatic odor characteristic of furan compounds.

Comment on solubility

Solubility of Dimethylbenzofurans

Dimethylbenzofurans, including compounds such as 2,4-dimethylbenzofuran, 3,6-dimethylbenzofuran, 4,7-dimethylbenzofuran, and 5,6-dimethylbenzofuran, exhibit varied solubility characteristics depending on their specific molecular structure and the presence of substituents. Here are some insights into their solubility:

  • Polarity: The presence of methyl groups does influence the overall polarity of these compounds, generally rendering them less polar than their unsubstituted counterparts. This characteristic affects how they interact with solvents.
  • Common Solvents: These compounds are typically soluble in organic solvents such as ethanol, acetone, and dichloromethane due to their nonpolar nature.
  • Water Solubility: Dimethylbenzofurans usually show limited solubility in water. This is primarily due to their hydrophobic aromatic nature, making them less favorable for hydration.
  • Temperature Effects: Solubility can also be influenced by temperature, with many organic compounds dissolving better at higher temperatures.

To summarize, the solubility of dimethylbenzofurans is characterized by:

  1. Low water solubility due to hydrophobic interactions.
  2. Good solubility in a range of organic solvents.
  3. Dependent on molecular structure and temperature conditions.

As a general rule, the more bulky and nonpolar the substituents, the less soluble these compounds will be in polar solvents like water.

Interesting facts

Interesting Facts about Dimethylbenzofurans

The dimethylbenzofurans are a fascinating class of organic compounds, derived from the fusion of a benzene ring and a furan ring with two methyl substituents. Among them, 2,4-dimethylbenzofuran, 3,6-dimethylbenzofuran, 4,7-dimethylbenzofuran, and 5,6-dimethylbenzofuran present unique structural and chemical properties. Here are some intriguing points about these compounds:

  • Diverse Isomerism: Each isomer exhibits its own distinct properties and reactivity due to the unique positions of the methyl groups on the benzofuran skeleton. This diversity can lead to different applications in various chemical reactions.
  • Applications in Organic Chemistry: Dimethylbenzofurans serve as important intermediates in the synthesis of pharmaceuticals and agrochemicals and are often explored in the development of organic light-emitting diodes (OLEDs).
  • Biological Activity: Preliminary studies suggest that some dimethylbenzofurans may exhibit biological activities. For instance, they have been investigated for potential anticancer properties and as anti-inflammatory agents.
  • Research Significance: The structural versatility of dimethylbenzofurans makes them valuable in material science and catalysis. The fine-tuning of their chemical properties through substituents can lead to better performing materials.
  • Synthetic Routes: These compounds can be synthesized through various methods, including the cyclization of substituted phenols and diols. Such synthetic routes highlight the creativity involved in organic synthesis.

In conclusion, dimethylbenzofurans embody a blend of structural complexity and functional potential that captivates chemists' interest. As research continues to unravel their properties and applications, these compounds are likely to pave the way for advancements in both synthetic organic chemistry and industrial applications.

Synonyms
25586-39-4
2,4-dimethyl-1-benzofuran;3,6-dimethyl-1-benzofuran;4,7-dimethyl-1-benzofuran;5,6-dimethyl-1-benzofuran