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2-Chloronitrobenzene

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Identification
Molecular formula
C6H4ClNO2
CAS number
88-73-3
IUPAC name
1-chloro-2-nitro-benzene;1-chloro-3-nitro-benzene;1-chloro-4-nitro-benzene
State
State
At room temperature, 2-Chloronitrobenzene is a solid that can sublimate slightly if left exposed to the air.
Melting point (Celsius)
34.50
Melting point (Kelvin)
307.65
Boiling point (Celsius)
245.00
Boiling point (Kelvin)
518.15
General information
Molecular weight
157.56g/mol
Molar mass
157.5560g/mol
Density
1.3040g/cm3
Appearence

The compound typically appears as a pale yellow crystalline solid. It is usually highly pure and can sometimes have a greenish tint due to impurities.

Comment on solubility

Solubility of 1-chloro-2-nitro-benzene, 1-chloro-3-nitro-benzene, and 1-chloro-4-nitro-benzene

The solubility of the chlorinated nitro-benzenes in various solvents is influenced by their molecular structure and interactions with the solvent molecules. These compounds exhibit differing solubilities based on the position of the nitro groups on the benzene ring, which can impact their overall polarity and hydrogen bonding capabilities.

Factors Affecting Solubility

  • Polarity: The presence of both chlorine and nitro groups increases the polarity of the molecules, making them more soluble in polar solvents such as ethanol and water.
  • Hydrophobic Interactions: Conversely, the aromatic nature of the benzene ring introduces hydrophobic characteristics, which allows some solubility in non-polar solvents like hexane.
  • Substituent Effects: The position of the nitro group significantly affects solubility:
    • 1-chloro-2-nitro-benzene - exhibits moderate solubility due to the proximity of the nitro and chloro groups.
    • 1-chloro-3-nitro-benzene - displays a unique balance of solubility from both groups being spaced apart.
    • 1-chloro-4-nitro-benzene - tends to have higher solubility due to enhanced resonance stabilization of the molecular structure.

General Solubility Characteristics

In summary, you can expect:

  • Polar solvents will often dissolve these compounds better due to their functional groups.
  • Solvent choice is crucial for achieving the desired dissolution behavior based on applications in chemical processes.
  • Temperature can also influence solubility; generally, higher temperatures increase solubility in solids.

Ultimately, while 1-chloro-2-nitro-benzene, 1-chloro-3-nitro-benzene, and 1-chloro-4-nitro-benzene all demonstrate similar solubility patterns, the nuances of their interactions with solvents warrant careful consideration in laboratory settings.

Interesting facts

Interesting Facts about 1-Chloro-2-nitrobenzene, 1-Chloro-3-nitrobenzene, and 1-Chloro-4-nitrobenzene

The compounds 1-chloro-2-nitrobenzene, 1-chloro-3-nitrobenzene, and 1-chloro-4-nitrobenzene are all important aromatic nitro compounds that showcase the diversity of substitution patterns on the benzene ring. Each of these compounds contains both a chloro group and a nitro group, but their varying positions lead to different chemical properties and reactions. Here are some fascinating aspects of these compounds:

  • Substituent Effects: The positioning of the chloro and nitro groups on the benzene ring significantly influences their reactivity. The electron-withdrawing nature of the nitro group can affect nucleophilic substitution reactions, making the chlorinated benzene more susceptible to further modifications.
  • Applications: These compounds are not just theoretical; they have practical applications in organic synthesis and the manufacture of pharmaceuticals, dyes, and agricultural chemicals. They serve as important intermediates in the production of various chemical products.
  • Environmental Concerns: While useful, the nitro groups in these compounds can lead to environmental issues due to their stability and persistence. Understanding their degradation pathways is crucial for mitigating their impact in contaminated sites.
  • Isomer Significance: The different isomers—meta and para—exhibit differing physical and chemical properties. This is a classic example of how structural isomerism can lead to varying characteristics, crucial for chemists when designing reactions or selecting materials.
  • Reactivities: These compounds can engage in various important reactions, such as electrophilic aromatic substitution, making them versatile in synthetic organic chemistry. For instance, the location of nitro substitution can direct further reactions to either ortho or para positions, yielding diverse products.

In summary, 1-chloro-2-nitrobenzene, 1-chloro-3-nitrobenzene, and 1-chloro-4-nitrobenzene exemplify the complexities and excitements of organic chemistry. Their diverse applications and behaviors not only enhance our understanding of aromatic compounds but also support innovation in chemical synthesis and industry.

Synonyms
SCHEMBL27630794