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Toluene derivatives

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Identification
Molecular formula
C8H9Br
IUPAC name
1-(bromomethyl)-2-methyl-benzene;1-(bromomethyl)-3-methyl-benzene;1-(bromomethyl)-4-methyl-benzene
State
State

These compounds are in a liquid state at room temperature. Being derivatives of toluene, they retain the characteristic aromaticity and volatility. The liquid is largely stable under standard conditions.

Melting point (Celsius)
-24.50
Melting point (Kelvin)
248.70
Boiling point (Celsius)
184.00
Boiling point (Kelvin)
457.20
General information
Molecular weight
171.04g/mol
Molar mass
171.0410g/mol
Density
1.2000g/cm3
Appearence

These toluene derivatives are colorless or lightly colored liquids at room temperature. They often have a sharp, sweet odor characteristic of many aromatic hydrocarbons. The liquid is typically clear and can appear slightly viscous.

Comment on solubility

Solubility of 1-(Bromomethyl)-2-methyl-benzene, 1-(Bromomethyl)-3-methyl-benzene, and 1-(Bromomethyl)-4-methyl-benzene

When discussing the solubility of the compounds 1-(bromomethyl)-2-methyl-benzene, 1-(bromomethyl)-3-methyl-benzene, and 1-(bromomethyl)-4-methyl-benzene, it is important to consider several factors that influence their behavior in different solvents:

  • Polarity: These compounds have a non-polar aromatic hydrocarbon structure due to the benzene ring, which makes them generally less soluble in polar solvents like water.
  • Hydrophobic Character: The presence of the bromomethyl group does introduce some polar characteristics, yet the overall hydrophobic nature of the aromatic rings predominates. Thus, they are better dissolved in non-polar organic solvents.
  • Solvent Compatibility: Each compound shows enhanced solubility in organic solvents such as:
    • Hexane
    • Chloroform
    • Toluene
  • Temperature Influence: Solubility can also vary with temperature, generally increasing with higher temperatures in organic solvents.

In summary, while these compounds are not soluble in water, they exhibit favorable solubility characteristics in organic solvents, making them suitable for various chemical applications. As a general rule, when asked about solubility, remember that like dissolves like—polar solvents dissolve polar substances, and non-polar solvents dissolve non-polar substances.

Interesting facts

Interesting Facts about 1-(bromomethyl)-2-methyl-benzene, 1-(bromomethyl)-3-methyl-benzene, and 1-(bromomethyl)-4-methyl-benzene

These three compounds—1-(bromomethyl)-2-methyl-benzene, 1-(bromomethyl)-3-methyl-benzene, and 1-(bromomethyl)-4-methyl-benzene—are interesting examples of brominated aromatic compounds. Each one is a derivative of toluene, where a bromomethyl group is added to the benzene ring at different positions, resulting in unique properties and reactivity.

Structural Analysis

  • The positions of the bromomethyl group significantly impact the compound's reactivity and interaction with other molecules.
  • In these compounds, the substitution pattern (ortho, meta, or para) can greatly influence physical and chemical properties.
  • The presence of the bromine atom provides sites for further chemical reactions, including substitution and elimination reactions.

Applications and Importance

All three of these bromomethyl derivatives find relevance in various chemical synthesis applications:

  • Intermediates: These compounds serve as important intermediates in the synthesis of more complex organic molecules.
  • Pharmaceuticals: The derivatives may play a role in the synthesis of drugs, particularly those that require specific functional groups.
  • Material Science: They may be utilized in developing advanced materials due to their unique chemical properties.

Reactivity and Mechanism

One of the fascinating aspects of these compounds is their reactivity:

  • They can undergo a variety of reactions such as nucleophilic substitutions due to the electrophilic nature of the bromomethyl group.
  • The different positions of the methyl group affect steric hindrance, leading to varying reaction rates and pathways.
  • Additionally, these compounds can participate in cross-coupling reactions, which are vital for constructing carbon-carbon bonds in organic synthesis.

Through the lens of scientific inquiry, understanding these compounds opens a pathway to exploring more complex chemistry phenomena while also emphasizing the significance of molecular structure in predicting chemical behavior. Whether you're a student or an experienced chemist, delving into these fascinating brominated benzene derivatives can enhance your understanding of organic chemistry.