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2-Chloronaphthalene-1,4-dione

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Identification
Molecular formula
C10H5ClO2
CAS number
101-90-6
IUPAC name
2-chloronaphthalene-1,4-dione
State
State

At room temperature, 2-Chloronaphthalene-1,4-dione is in a solid state. It is usually stable and moldable under standard conditions.

Melting point (Celsius)
173.00
Melting point (Kelvin)
446.15
Boiling point (Celsius)
308.00
Boiling point (Kelvin)
581.15
General information
Molecular weight
192.60g/mol
Molar mass
192.5960g/mol
Density
1.5096g/cm3
Appearence

2-Chloronaphthalene-1,4-dione typically appears as a yellow solid crystalline substance. It is notable for its bright color and is usually available in a powdered or crystalline form.

Comment on solubility

Solubility of 2-chloronaphthalene-1,4-dione

2-chloronaphthalene-1,4-dione, a member of the naphthoquinone family, exhibits intriguing solubility characteristics. Understanding the solubility of this compound is essential for its applications in various fields, including organic synthesis and material science.

Solubility Insights

  • 2-chloronaphthalene-1,4-dione is known to be soluble in organic solvents such as ethanol, ethyl acetate, and chloroform.
  • It demonstrates limited solubility in water, which is typical for many aromatic compounds due to their nonpolar characteristics.
  • The presence of the −Cl substituent and the −C=O functional groups affects its interaction with solvents.
  • According to solubility principles, the "like dissolves like" rule plays an essential role, indicating that nonpolar solvents will dissolve nonpolar solutes more effectively.

In practical terms, this means that while 2-chloronaphthalene-1,4-dione may not readily mix with polar solvents such as water, it can easily dissolve in various nonpolar or moderately polar organic solvents, which can be advantageous during synthetic processes.


As with many compounds, proper handling and understanding of solubility can lead to improved outcomes in research and applications. As a chemist, one might say: "Grasping the solubility profile is the key to unlocking the potential of chemical compounds."

Interesting facts

Interesting Facts About 2-Chloronaphthalene-1,4-dione

2-Chloronaphthalene-1,4-dione is a fascinating compound with several noteworthy aspects that make it a subject of interest for chemists and chemical enthusiasts alike.

1. Chemical Structure and Properties

  • The compound features a naphthalene ring system, which is important in organic chemistry for its stability and reactivity.
  • The presence of a chlorine atom introduces interesting electronic effects that can influence reactivity and interactions with other compounds.
  • As an example of a diketone, it has two ketone functional groups, making it a valuable substrate in various synthetic applications.

2. Applications in Synthesis

  • 2-Chloronaphthalene-1,4-dione serves as a versatile building block in organic synthesis, especially in creating more complex chemical entities.
  • It is used in the synthesis of various pharmaceuticals and agrochemicals, highlighting its utility in industries that require organic compounds with specific functionality.

3. Insights into Reactivity

Due to the unique positioning of its functional groups, this compound exhibits interesting reactivity patterns:

  • It can undergo various nucleophilic addition reactions, which are crucial in forming new carbon-carbon bonds.
  • The chlorine substituent may also facilitate substitution reactions, making it easier to modify the compound for specific chemical purposes.

4. Environmental Considerations

As with many compounds containing halogens, 2-chloronaphthalene-1,4-dione may pose certain environmental concerns:

  • Research in the field of environmental chemistry focuses on the persistence of halogenated compounds and their potential toxicity.
  • Understanding how this compound interacts with biological systems is essential for assessing its safety and environmental impact.

In summary, 2-chloronaphthalene-1,4-dione is not only significant for its chemical properties but also for its applications and implications in both synthetic chemistry and environmental science. Its intriguing structure and reactivity make it a point of interest for future research and development!

Synonyms
2-Chloro-1,4-naphthoquinone
1010-60-2
2-chloronaphthalene-1,4-dione
2-Chloronaphthoquinone
NSC 400597
1,4-NAPHTHOQUINONE, 2-CHLORO-
UNII-FOF3PSJ59Z
FOF3PSJ59Z
EINECS 213-776-2
BRN 1867045
CHEBI:28160
NSC-400597
DTXSID00143623
4-07-00-02425 (Beilstein Handbook Reference)
chloro-K3
DTXCID5066114
213-776-2
cctjhvltajtpbv-uhfffaoysa-n
1,4-Naphthalenedione, 2-chloro-
MFCD00029187
2-Chloro-1,4-naphthalenedione
2-chloro-1,4-dihydronaphthalene-1,4-dione
2-Chloronaphthalene-1,4-dione (2-Chloro-1,4-naphthoquinone)
chloronaphthoquinone
2-Chlor-1,4-naphthochinon
2-chloro-1,4-naphthquinone
SCHEMBL917548
CHEMBL349147
WLN: L66 BV EVJ CG
2-Chloro-[1,4]Naphthoquinone
FD7245
NSC400597
AKOS006343761
GS-3324
AC-15235
DA-49387
PD099119
SY051032
HY-115243
C2721
CS-0034824
NS00023017
C03753
EN300-6490914
Q27103536