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2-Chlorocyclohexanone

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Identification
Molecular formula
C6H9ClO
CAS number
822-86-6
IUPAC name
2-chlorocyclohexanone
State
State

At room temperature, 2-Chlorocyclohexanone is in a liquid state. It remains stable under normal conditions but should be stored properly to prevent any decomposition.

Melting point (Celsius)
-12.00
Melting point (Kelvin)
261.15
Boiling point (Celsius)
198.00
Boiling point (Kelvin)
471.15
General information
Molecular weight
132.58g/mol
Molar mass
132.5830g/mol
Density
1.1380g/cm3
Appearence

2-Chlorocyclohexanone is a colorless to pale yellow liquid. It may have a slight odor characteristic of ketones, and it is typically clear and free-flowing. The compound should be handled carefully as it can react with strong oxidizers.

Comment on solubility

Solubility of 2-chlorocyclohexanone

2-chlorocyclohexanone is an intriguing compound when it comes to solubility. Its unique structure contributes to its solubility characteristics, which can be summarized as follows:

  • Polarity: Due to the presence of the carbonyl group and chlorine atom, 2-chlorocyclohexanone possesses moderate polarity.
  • Solvent Compatibility: It typically exhibits good solubility in polar organic solvents such as ethanol and acetone while displaying limited solubility in water.
  • Hydrophobic Effects: The cyclohexane ring contributes to hydrophobic interactions, which can limit water solubility.

Overall, while 2-chlorocyclohexanone is not soluble in water, it finds a welcoming environment in various organic solvents. As a general rule, compounds with higher polarity will tend to dissolve better in polar solvents, thus reinforcing the adage: "Like dissolves like." The solubility of 2-chlorocyclohexanone makes it valuable in specific applications within organic synthesis and pharmaceutical formulations.

Interesting facts

Interesting Facts about 2-Chlorocyclohexanone

2-Chlorocyclohexanone is an intriguing compound that belongs to the class of ketones. Here are some captivating aspects of this chemical:

  • Structure and Isomerism: This compound features a chlorinated cyclohexanone structure, allowing for unique geometries due to its cyclic nature. The chlorine atom introduces interesting stereochemical elements, making it an ideal candidate for studying regioselectivity.
  • Applications in Synthesis: 2-Chlorocyclohexanone serves as a versatile intermediate in organic synthesis. It can be utilized in the preparation of various pharmaceuticals and agrochemicals, showcasing the importance of chlorinated compounds in the development of new drugs.
  • Mechanistic Studies: Chemists often use 2-chlorocyclohexanone in mechanistic studies of nucleophilic substitution reactions. The behavior of the chlorine atom can be closely analyzed, providing insights into reaction kinetics and pathways.
  • Biological Relevance: Chlorinated compounds, including 2-chlorocyclohexanone, have been studied for their biological activity. Understanding how such compounds interact within biological systems can lead to discoveries in medicinal chemistry.
  • Challenges in Handling: While it has valuable applications, safety must be prioritized due to potential toxicity. Proper handling protocols are essential, and it presents an opportunity for students to learn about chemical safety measures in laboratory environments.

As this compound continues to be a subject of academic and industrial interest, ongoing research is likely to unveil even more fascinating aspects. The world of chlorinated ketones, particularly 2-chlorocyclohexanone, promises to remain dynamic and significant.

Synonyms
2-Chlorocyclohexanone
822-87-7
CYCLOHEXANONE, 2-CHLORO-
alpha-Chlorocyclohexanone
2-Chlorocyclohexonone
.alpha.-Chlorocyclohexanone
EINECS 212-505-5
NSC 12439
UNII-1134E5H2KV
DTXSID1021530
1134E5H2KV
NSC-12439
DTXCID001530
212-505-5
(+-)-2-chloro-1-cyclohexanone
(+-)-2-chlorocyclohexanone
2-chlorocyclohexanone, (+-)-
cchnwurrbfgqcd-uhfffaoysa-n
2-chlorocyclohexan-1-one
MFCD00001626
(+/-)-2-CHLOROCYCLOHEXANONE
2-CHLOROCYCLOHEXANONE, (+/-)-
(+/-)-2-CHLORO-1-CYCLOHEXANONE
2-chloro-cyclohexanone
2-chloro-1-cyclohexanone
2-chlorocyclohexanon
2-chlorocylohexanone
2-chloro cyclohexanone
WLN: L6VTJ BG
2-chloro-cyclohexan-1-one
2-Chlorocyclohexanone, 98%
SCHEMBL186361
CHEMBL3183260
NSC12439
Tox21_200522
AC1582
BBL011103
STK802347
AKOS001133267
AKOS016889127
CS-W013402
NCGC00248671-01
NCGC00258076-01
AS-57502
CAS-822-87-7
SY038921
DB-056596
NS00022820
EN300-18889
Q27251237
Z94598693
F0001-2107
2-Chlorocyclohexanone stabilized over calcium carbonate/magnesium oxide