Skip to main content

1,2-dimethyl-3-nitrobenzene

ADVERTISEMENT
Identification
Molecular formula
C8H9NO2
CAS number
C6H4(NO2)(CH3)2
IUPAC name
1,2-dimethyl-3-nitro-benzene;1,3-dimethyl-2-nitro-benzene;1,3-dimethyl-5-nitro-benzene;1,4-dimethyl-2-nitro-benzene;2,4-dimethyl-1-nitro-benzene
State
State

At room temperature, 1,2-dimethyl-3-nitrobenzene is a solid, typically appearing as yellow crystals or powder.

Melting point (Celsius)
12.00
Melting point (Kelvin)
285.15
Boiling point (Celsius)
239.00
Boiling point (Kelvin)
512.15
General information
Molecular weight
151.16g/mol
Molar mass
151.1640g/mol
Density
1.1060g/cm3
Appearence

1,2-Dimethyl-3-nitrobenzene appears as a yellow solid. It is typically crystalline in nature and has a characteristic odor.

Comment on solubility

Solubility of Nitrobenzene Derivatives

The solubility of nitrobenzene derivatives, such as 1,2-dimethyl-3-nitro-benzene, 1,3-dimethyl-2-nitro-benzene, 1,3-dimethyl-5-nitro-benzene, 1,4-dimethyl-2-nitro-benzene, and 2,4-dimethyl-1-nitro-benzene, can vary significantly due to their unique structural characteristics. Each compound's solubility properties can be influenced by the following factors:

  • Presence of Nitro Groups: The nitro group (-NO2) is a strong electron-withdrawing group, which enhances the polarity of the aromatic ring and affects its solubility in polar solvents.
  • Methyl Substitution: Methyl groups (-CH3) can introduce steric hindrance. Their positioning (ortho, meta, or para) can either enhance or reduce interaction with solvent molecules.
  • Solvent Type: These compounds generally exhibit higher solubility in organic solvents compared to water due to their hydrophobic aromatic structures.
  • Hydrogen Bonding: The ability of these compounds to engage in hydrogen bonding can influence their solubility; compounds that can act as hydrogen bond donors or acceptors often show better solubility.

It is generally observed that the nitrobenzene derivatives are more soluble in organic solvents such as acetone and ether than in water. However, specific solubility measures will depend on the specific structure and substituents of each compound. As a rule of thumb, "like dissolves like" is a helpful guideline—polar compounds are more soluble in polar solvents, while nonpolar compounds prefer nonpolar solvents.

Understanding these solubility characteristics is essential for applications in various fields, including organic synthesis and pharmaceuticals, where the choice of solvent can significantly impact the efficiency of reactions.

Interesting facts

Interesting Facts about Dimethyl Nitrobenzenes

Dimethyl nitrobenzenes are a fascinating group of aromatic compounds that combine the characteristics of both dimethyl groups and nitro substituents on a benzene ring. Here are some intriguing facts about these compounds:

Chemical Structure

  • The compounds consist of a benzene ring with two methyl groups (–CH3) and one nitro group (–NO2) substituting hydrogen atoms, in various positions.
  • The specific arrangement of these groups significantly affects the chemical and physical properties, including their reactivity, solubility, and stability.

Applications

  • These compounds are often used as intermediates in the synthesis of dyes, pharmaceuticals, and agrochemicals, highlighting their importance in various industrial sectors.
  • In organic synthesis, they serve as key building blocks due to their reactivity with other chemical agents, making them valuable in the development of more complex structures.

Environmental Impact and Toxicity

  • These nitrobenzenes can pose environmental risks; they are known to be persistent in the environment and can bioaccumulate.
  • Some members of this group are toxic and require careful handling in laboratories and industrial settings, emphasizing the need for stringent safety protocols.

Scientific Interest

  • Researchers are interested in the electronic effects of the nitro group and how it influences the reactivity of adjacent carbon atoms on the benzene ring.
  • studies may focus on the isomeric forms, where each configuration can exhibit unique properties, leading to diverse applications.

In conclusion, 1,2-dimethyl-3-nitro-benzene, 1,3-dimethyl-2-nitro-benzene, 1,3-dimethyl-5-nitro-benzene, 1,4-dimethyl-2-nitro-benzene, and 2,4-dimethyl-1-nitro-benzene showcase the intricate interplay between structure and function in organic chemistry. Their synthesis and application continue to be an exciting field of study for both scientists and students alike.