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1,3,5-tribromo-2-methylbenzene

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Identification
Molecular formula
C7H5Br3
CAS number
607-95-4
IUPAC name
1,2,3-tribromo-5-methyl-benzene;1,2,5-tribromo-3-methyl-benzene;1,3,5-tribromo-2-methyl-benzene
State
State

At room temperature, it is in a solid state.

Melting point (Celsius)
66.00
Melting point (Kelvin)
339.15
Boiling point (Celsius)
275.00
Boiling point (Kelvin)
548.15
General information
Molecular weight
314.82g/mol
Molar mass
314.8240g/mol
Density
2.1165g/cm3
Appearence

This compound appears as a colorless, crystalline substance. It is typically in the form of solid crystals that are not easily dissolved in water.

Comment on solubility

Solubility of 1,2,3-tribromo-5-methyl-benzene, 1,2,5-tribromo-3-methyl-benzene, and 1,3,5-tribromo-2-methyl-benzene

When considering the solubility of the tri-bromo substituted methyl-benzene derivatives, there are a few pivotal aspects to keep in mind:

  • Polarity: The presence of bromine atoms, which are highly electronegative, significantly influences the overall polarity of each compound. These compounds tend to be more polar than their non-bromo analogs.
  • Solvent Interaction: These compounds generally exhibit greater solubility in non-polar solvents such as hexane and toluene, owing to their hydrocarbon-like characteristics.
  • Hydrogen Bonding: The ability for these molecules to engage in hydrogen bonding is limited due to the lack of -OH or -NH groups. This can reduce solubility in polar solvents like water.
  • Effect of Substituents: The position of the methyl and bromo substituents can further modify their solubility attributes. For example, steric hindrance from bulky bromine groups might hinder solvation.

In essence, it can be concluded that while these compounds are more soluble in non-polar solvents due to their hydrophobic characteristics, their solubility in polar solvents remains limited due to the interplay of polarity, molecular structure, and the lack of functional groups that enhance solubility.

“Understanding solubility is as critical as understanding reactivity in the study of organic compounds.”

Interesting facts

Interesting Facts About Tribromo-Methylbenzenes

The tribromo-methylbenzenes consist of several isomers, including 1,2,3-tribromo-5-methyl-benzene, 1,2,5-tribromo-3-methyl-benzene, and 1,3,5-tribromo-2-methyl-benzene. These compounds are interesting due to their unique structural configurations and potential applications in various fields.

Key Points

  • Halogenation: Each of these compounds features three bromine atoms, resulting from the halogenation of methylbenzene (toluene). This contributes to their chemical reactivity, particularly in substitution reactions.
  • Environmental Considerations: Tribromo compounds, due to the presence of bromine, may have implications in environmental chemistry and toxicology. Some brominated organic compounds can be persistent in the environment and may pose ecological risks.
  • Applications: They are used as intermediates in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. Their unique properties allow chemists to manipulate and utilize them in various synthetic pathways.
  • Isomeric Diversity: The presence of multiple isomers highlights the diversity of substitution patterns in aromatic compounds. This can lead to varying chemical and physical properties, making the study of these isomers particularly intriguing.

As noted by chemists, "The arrangement of substituents on a benzene ring significantly influences the reactivity and properties of the compound." This principle is readily observable in the tribromo-methylbenzenes, where slight changes in the position of bromine or methyl groups can lead to different reactivity patterns.

Overall, tribromo-methylbenzenes serve as a fascinating subject of study, shedding light on the interplay of structure and reactivity in organic chemistry.

Synonyms
TRIBROMOTOLUENE
27476-22-8
SCHEMBL29844353
DTXSID80181902