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Cyclopentadiene

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Identification
Molecular formula
C5H6
CAS number
542-92-7
IUPAC name
cyclopenta-1,3-diene
State
State

At room temperature, cyclopentadiene is a volatile liquid. Due to its tendency to dimerize, it can sometimes transition into a solid form (dicyclopentadiene) if not handled or stored properly. In its purified form, it remains a liquid, but it requires caution in handling to prevent polymerization.

Melting point (Celsius)
-97.00
Melting point (Kelvin)
176.15
Boiling point (Celsius)
42.50
Boiling point (Kelvin)
315.65
General information
Molecular weight
66.10g/mol
Molar mass
66.1010g/mol
Density
0.8020g/cm3
Appearence

Cyclopentadiene is a colourless liquid with a strong, sharp odor. It is highly volatile and tends to dimerize at room temperature, so it is often freshly distilled before use. The liquid may appear slightly yellowish due to impurities or partial dimerization.

Comment on solubility

Solubility of Cyclopenta-1,3-diene

Cyclopenta-1,3-diene (C5H6) is an intriguing compound known for its unique structure and chemical properties. When it comes to solubility, several factors play a significant role:

  • Polarity: Cyclopenta-1,3-diene is a non-polar molecule due to its symmetrical structure and distribution of electrons. This characteristic influences its solubility patterns.
  • Solvent Compatibility: Generally, non-polar compounds such as cyclopenta-1,3-diene are soluble in non-polar solvents. Some common examples include:
    • Hexane
    • Benzene
    • Toluene
  • Water Solubility: It is important to note that cyclopenta-1,3-diene is insoluble in water, a polar solvent, due to the principle of "like dissolves like."

In conclusion, solubility in cyclopenta-1,3-diene is primarily influenced by its non-polar nature, making it compatible with non-polar solvents while remaining insoluble in polar environments such as water.

Interesting facts

Interesting Facts about Cyclopenta-1,3-diene

Cyclopenta-1,3-diene is a fascinating diene compound that primarily belongs to the category of unsaturated hydrocarbons. Its unique structure features a five-membered carbon ring with two double bonds positioned at the 1 and 3 carbon atoms, which contributes to its interesting reactivity and properties. Here are some remarkable aspects of this compound:

  • Reactivity: Cyclopenta-1,3-diene is known for its high reactivity due to the presence of conjugated double bonds. This makes it a useful starting material for various synthetic reactions, including Diels-Alder reactions, which are essential in organic chemistry for constructing complex molecules.
  • Ionization: The compound can easily form cationic intermediates, allowing for the exploration of new synthetic pathways that harness these reactive species. Its cationic form can lead to the development of various polycyclic hydrocarbons.
  • Applications: Cyclopenta-1,3-diene has important applications in organic synthesis and materials science. It can act as a precursor in the production of advanced polymers and materials, showcasing its versatility in industrial contexts.
  • Historical Significance: The study of cyclopenta-1,3-diene has provided insights into the understanding of resonance and stabilization in organic molecules. The compound has been the subject of numerous studies, emphasizing its role in advancing organic chemistry knowledge.

As a student or enthusiast in chemistry, you may find it intriguing that compound behavior is closely linked to its structure. The presence of double bonds in cyclopenta-1,3-diene leads to unique electronic properties that can greatly affect reaction pathways. This illustrates the incredible connection between molecular geometry and chemical reactivity, a fundamental concept within the discipline!

Synonyms
Cyclopentadiene
1,3-CYCLOPENTADIENE
cyclopenta-1,3-diene
542-92-7
Pyropentylene
Pentole
R-Pentine
HSDB 2514
EINECS 208-835-4
UNII-5DFH9434HF
5DFH9434HF
26912-33-4
DTXSID0027191
CHEBI:30664
DTXCID007191
EC 208-835-4
cyclopentadien
cyclo pentadiene
cyclo-pentadiene
CYCLOPENTADIENE [MI]
ghl.PD_Mitscher_leg0.1205
CHEMBL3188826
1,3-CYCLOPENTADIENE [HSDB]
Tox21_302134
AKOS025295445
AT31522
NCGC00255341-01
CAS-542-92-7
DB-013019
NS00006170
1.3-cyclopentadiene pound Dimer form pound(c)
A818675
Q424390
Q2209035
InChI=1/C5H6/c1-2-4-5-3-1/h1-4H,5H
208-835-4