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Norbornadiene

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Identification
Molecular formula
C7H8
CAS number
121-46-0
IUPAC name
bicyclo[2.2.1]hepta-2,5-diene
State
State

Norbornadiene is found in a liquid state at room temperature. Its viscous nature is characteristic of hydrocarbons with similar carbon-skeleton structures.

Melting point (Celsius)
-36.40
Melting point (Kelvin)
236.75
Boiling point (Celsius)
89.00
Boiling point (Kelvin)
362.15
General information
Molecular weight
92.14g/mol
Molar mass
92.1380g/mol
Density
0.9096g/cm3
Appearence

Norbornadiene is a colorless liquid at room temperature. It possesses a distinctive smell that is similar to that of camphor or related bicyclic compounds. When pure, it is generally clear and free of impurities, but it can appear slightly yellow if impure or aged due to oxidation.

Comment on solubility

Solubility of Bicyclo[2.2.1]hepta-2,5-diene

Bicyclo[2.2.1]hepta-2,5-diene is a unique compound that exhibits fascinating solubility properties. Its solubility is influenced by several factors:

  • Polarity: Bicyclo[2.2.1]hepta-2,5-diene is a nonpolar molecule, making it poorly soluble in polar solvents such as water.
  • Solvent Compatibility: It tends to dissolve well in nonpolar organic solvents, including:
    1. Hexane
    2. Toluene
    3. Chloroform
  • Temperature Effects: Like many organic compounds, solubility may increase with temperature, allowing for better dispersion in nonpolar solvents.

In summary, while bicyclo[2.2.1]hepta-2,5-diene is insoluble in water, it readily dissolves in various nonpolar organic solvents, which can be crucial for its applications in organic chemistry and materials science.

Interesting facts

Interesting Facts about Bicyclo[2.2.1]hepta-2,5-diene

Bicyclo[2.2.1]hepta-2,5-diene is a fascinating compound that belongs to the family of bicyclic hydrocarbons. Its structure presents several noteworthy features that capture the interest of chemists and students alike.

Unique Structure

  • Bicyclic Nature: The compound consists of two interconnected rings, providing an intriguing framework for various chemical reactions.
  • Ring Strain: The unique geometry introduces significant ring strain, which can influence its reactivity compared to other hydrocarbons.
  • Diene Characteristics: As a diene, it contains two double bonds, positioning it for interesting electrophilic addition reactions.

Chemical Behavior

  • Reactivity: Bicyclo[2.2.1]hepta-2,5-diene can undergo various reactions typical for dienes, such as Diels-Alder cycloadditions, demonstrating its utility in synthetic chemistry.
  • Isomerism: It exhibits geometric isomerism due to the presence of double bonds, offering a rich field for studying stereochemistry.

Practical Applications

The compound’s distinctive properties make it a valuable topic for research in organic synthesis and materials science. Its derivatives have potential applications in:

  • Polymer Chemistry: Understanding its behavior can contribute to developing new polymeric materials.
  • Pharmaceuticals: Exploring how such unique structures can act as pharmaceutical intermediates.

In summary, bicyclo[2.2.1]hepta-2,5-diene is not just an ordinary hydrocarbon; it embodies intriguing structural characteristics and reactivity patterns that continue to inspire chemists. As noted by chemist J. K. Hwang, "The complexity of molecular structures often leads to unexpected reactivity and applications."

Synonyms
2,5-Norbornadiene
Bicyclo[2.2.1]hepta-2,5-diene
121-46-0
Norbornadiene
BICYCLO(2.2.1)HEPTA-2,5-DIENE
NSC 13672
UN2251
UNII-W9ZTQ75ZUS
2,5-Norbornadiene (stabilized with BHT)
W9ZTQ75ZUS
Bicyclo(2.2.1)heptadiene
EINECS 204-472-0
AI3-24887
NSC-13672
NORBORNADIENE [MI]
DTXSID1059523
3,6-Methano-1,4-cyclohexadiene
Bicyclo[2.2.1]-2,5-heptadiene
MFCD00082301
16422-76-7
UN-2251
Bicyclo[2.2.1]heptadiene
NBD
Bicyclo(2.2.1)-2,5-heptadiene
Dicycloheptadiene
8,9,10-Trinorborna-2,5-diene
BICYCLO(2.2.1)HEPTA-2,5-DIENE, STABILIZED
BICYCLO[2.2.1]HEPTA-2,5-DIENE, STABILIZED
2,5Norbornadiene, inhibited
3,6Methano1,4cyclohexadiene
8,9,10Trinorborna2,5diene
Bicyclohepta2,5diene, inhibited
Bicyclo(2.2.1)hepta2,5diene
DTXCID6033669
NSC13672
NSC167540
STL453640
2,5-NORBORNADIENE, STABILIZED
AKOS005145646
AKOS015912918
AKOS016008675
bicyclo-(2,2,1)-hepta-2,5-diene
NSC-167540
Bicyclo[2.2.1]hepta-2,5-diene, 98%
2,5-Norbornadiene, (stabilized with BHT)
DB-243109
N0346
NS00023960
Bicyclo[2.2.1]hepta-2, dimer, stereoisomer
EN300-93414
bicyclo[2.2.1]hepta-2,5-diene,(Norbornadiene)
Q726795
Bicyclo(2,2,1)hepta-2,5-diene, inhibited or 2,5-Norborandiene, inhibited
3,6-Methano-1,4-cyclohexadiene; Bicyclo[2.2.1]heptadiene; NSC 13672; Norbornadiene;
204-472-0
Bicyclo(2,2,1)hepta-2,5-diene, inhibited or 2,5-Norborandiene, inhibited [UN2251] [Flammable liquid]