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Toluene chlorides

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Identification
Molecular formula
C7H7Cl
CAS number
95-49-8; 108-41-8; 106-43-4
IUPAC name
1-chloro-2-methyl-benzene;1-chloro-3-methyl-benzene;1-chloro-4-methyl-benzene
State
State

These compounds are typically in a liquid state at room temperature. They are volatile and have low melting points, hence they are stored in tightly closed containers to prevent evaporation.

Melting point (Celsius)
-35.00
Melting point (Kelvin)
238.15
Boiling point (Celsius)
157.90
Boiling point (Kelvin)
431.05
General information
Molecular weight
126.59g/mol
Molar mass
126.5820g/mol
Density
0.9994g/cm3
Appearence

1-Chloro-2-methylbenzene, 1-Chloro-3-methylbenzene, and 1-Chloro-4-methylbenzene are colorless liquids. These compounds are also known individually as ortho-Chlorotoluene, meta-Chlorotoluene, and para-Chlorotoluene, respectively. They possess a characteristic aromatic odor typical of chlorinated aromatic compounds. Their appearance doesn't vary significantly among the isomers.

Comment on solubility

Solubility of 1-Chloro-2-methyl-benzene, 1-Chloro-3-methyl-benzene, and 1-Chloro-4-methyl-benzene

1-Chloro-2-methyl-benzene, 1-chloro-3-methyl-benzene, and 1-chloro-4-methyl-benzene, known as ortho-, meta-, and para-chlorotoluene respectively, exhibit notable differences in solubility due to their molecular structures and the spatial arrangement of functional groups. Here's a more in-depth look:

  • Solubility in Water: All three compounds are generally poorly soluble in water. This characteristic is primarily attributed to their non-polar hydrocarbon ring structure which does not interact favorably with polar water molecules.
  • Solubility in Organic Solvents: These compounds are much more soluble in organic solvents such as:
    • Toluene
    • Hexane
    • Acetone
  • Effect of Substitution: The position of the chlorine atom in relation to the methyl group can subtly influence solubility. For example:
    • Ortho-Chlorotoluene: This variant tends to have slightly different intermolecular interactions, affecting its solubility dynamics.
    • Meta- and Para-Chlorotoluene: These substitutions benefit from greater symmetry, impacting their volatility and solubility in organic solvents.

In summary, while all three isomers of chlorotoluene are sparingly soluble in water, they demonstrate a significantly higher solubility in a range of organic solvents. Therefore, understanding the solubility properties of these compounds is crucial for their application in various chemical processes and industries.

Interesting facts

Interesting Facts about Chlorotoluene Compounds

Chlorotoluenes are a fascinating group of chemical compounds that consist of a chlorinated benzene ring with a methyl group attached. These compounds are commonly referred to as ortho-chlorotoluene, meta-chlorotoluene, and para-chlorotoluene, representing the positions of the chlorine and methyl groups. Here are some interesting insights into these compounds:

  • Industrial Applications: Chlorotoluenes are widely used in various industrial applications, especially as solvents and intermediates in the synthesis of chemicals.
  • Organic Synthesis: They play an important role in organic synthesis, serving as precursors for the production of pharmaceuticals, dyes, and agrochemicals.
  • Environment and Safety: Due to the presence of chlorine, chlorotoluenes require careful handling. They can be hazardous to health and the environment, emphasizing the need for stringent safety protocols in their use.
  • Isomeric Nature: The three isomers of chlorotoluenes exhibit different chemical properties and behaviors, largely influenced by the positions of the chlorine and methyl groups. For example, ortho-chlorotoluene can exhibit different reactivity compared to para-chlorotoluene.
  • Research Potential: Ongoing research into chlorotoluenes focuses on their environmental impact and the development of safer alternatives that retain their desirable chemical properties.

In summary, chlorotoluene compounds not only showcase the intricate beauty of organic chemistry but also highlight the balance between utility and environmental responsibility in the scientific community. Their unique structures and properties make them a subject of ongoing interest for chemists and industry professionals alike.

Synonyms
SCHEMBL26727