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Norbornadiene information


Norbornadiene
Names
Preferred IUPAC name
Bicyclo[2.2.1]hepta-2,5-diene
Other names
2,5-Norbornadiene
Identifiers
CAS Number
  • 121-46-0 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8160
ECHA InfoCard 100.004.066 Edit this at Wikidata
EC Number
  • 204-472-0
PubChem CID
  • 8473
UNII
  • W9ZTQ75ZUS checkY
UN number 2251
CompTox Dashboard (EPA)
  • DTXSID1059523 Edit this at Wikidata
InChI
  • InChI=1S/C7H8/c1-2-7-4-3-6(1)5-7/h1-4,6-7H,5H2
    Key: SJYNFBVQFBRSIB-UHFFFAOYSA-N
SMILES
  • C1C2C=CC1C=C2
Properties
Chemical formula
C7H8
Molar mass 92.14 g/mol
Density 0.906 g/cm3
Melting point −19 °C (−2 °F; 254 K)
Boiling point 89 °C (192 °F; 362 K)
Solubility in water
Insoluble
Hazards
GHS labelling:
Pictograms
GHS02: Flammable
Signal word
Danger
Hazard statements
H225
Precautionary statements
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. It has been intensively studied owing to its high reactivity and distinctive structural property of being a diene that cannot isomerize (isomers would be anti-Bredt alkenes). Norbornadiene is also a useful dienophile in Diels-Alder reactions.

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Norbornadiene

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Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for...

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Tetrazine

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of importance as a reagent in Diels-Alder reactions. It reacts with norbornadiene in a sequence of one DA reaction and two retro-DA reactions to cyclopentadiene...

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Photoisomerization

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presence of a catalyst, norbornadiene converts to quadricyclane via ~300nm UV radiation . When converted back to norbornadiene, quadryicyclane’s ring strain...

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Dieldrin

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Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene. Originally developed in the 1940s as...

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Alicyclic compound

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cycloheptene, cyclooctene, and so on. Bicyclic alkenes include norbornene and norbornadiene. Two more examples are shown below, methylenecyclohexane on the left...

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C7H8

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(molar mass: 92.14 g/mol) may refer to: Cycloheptatriene Isotoluenes Norbornadiene Quadricyclane Toluene, or toluol This set index page lists chemical...

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Quadricyclane

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is higher for freshly distilled norbornadiene, but commercial reagents will suffice. The conversion of norbornadiene into quadricyclane is achieved with...

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Organoruthenium chemistry

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the metal centre: The compound Ru(COD)(COT) is capable of dimerizing norbornadiene: Multinuclear organo-ruthenium complexes have been investigated for...

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Chromium hexacarbonyl

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labile adducts, including labile but complexes with some noble gases. Norbornadiene was dimerized photochemically in the presence of Cr(CO)6, similarly...

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Norbornane

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groups from the parent molecule bornane. 2-Norbornyl cation Norbornene Norbornadiene Bornane endo-Norborneol exo-Norborneol Norcamphor, the ketone derivative...

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Cycloaddition

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dipolar reaction both become a [4+2]cycloaddition. The reaction between norbornadiene and an activated alkyne is a [2+2+2]cycloaddition. The Diels-Alder reaction...

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Transition metal alkene complex

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adducts with many zero-valent metals. Butadiene, cyclooctadiene, and norbornadiene are well-studied chelating agents. Trienes and even some tetraenes can...

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Solar chemical

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The norbornadiene-quadricyclane couple and its derivatives have been extensively investigated for solar energy storage processes. Norbornadiene is converted...

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Norbornene

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norbornenes can be prepared similarly. Related bicyclic compounds are norbornadiene, which has the same carbon skeleton but with two double bonds, and norbornane...

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Triazine

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to form pyridine rings. An alternative to using an alkyne is to use norbornadiene which can be thought of as a masked alkyne. In 2007, a method for synthesizing...

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Diene

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(notice that each double bond is two carbons away from the other). E: Norbornadiene, a strained bicyclic and unconjugated diene. F: Dicyclopentadiene....

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Thermal energy storage

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into its original isomer). A promising candidate for such a MOST is Norbornadiene (NBD). This is because there is a high energy difference between the...

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Iron pentacarbonyl

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replaced by two olefins. Many dienes undergo this reaction, notably norbornadiene and 1,3-butadiene. One of the more historically significant derivatives...

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Oxanorbornadiene

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carbons of 1,4-cyclohexadiene. OND is related to all-carbon bicycle norbornadiene. While unsubstituted OND is known, the most useful OND derivatives are...

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Energy storage

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have been proposed as energy storage solutions. The organic compound norbornadiene converts to quadricyclane upon exposure to light, storing solar energy...

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List of organic reactions

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"Bridged Ring Compounds. X.1,2 The Reaction of Benzenesulfonyl Azide with Norbornadiene, Dicyclopentadiene, and Bicyclo[2.2.2]-2-octene". The Journal of Organic...

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Cyclopentadienylcobalt dinitrosyl

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enantiomeric excess. This methodology was expanded to diene substrates such as norbornadiene. These ring strained dienes allowed for sequential, stereoselective...

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NBD

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binomial distribution Network block device Neurobiological brain disorder Norbornadiene, a bicyclic hydrocarbon This disambiguation page lists articles associated...

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Aldrin

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Aldrin is synthesized by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct. In 1967, the composition...

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Olefin metathesis

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followed in 1993 With a Schrock catalyst modified with a BINOL ligand in a norbornadiene ROMP leading to highly stereoregular cis, isotactic polymer. Alkane...

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Organic azide

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non-polar. Another azide regular is tosyl azide here in reaction with norbornadiene in a nitrogen insertion reaction: Some azides are valuable as bioorthogonal...

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Bioorthogonal chemistry

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candidate screen based on reactivity. To prevent light-induced reversion to norbornadiene, diethyldithiocarbamate is added to chelate the nickel in the product...

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Ring strain

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"Ring Strain Energies: Substituted Rings, Norbornanes, Norbornenes and Norbornadienes". Tetrahedron. 60: 8103– 8112. Wiberg, K. B. (1968). "Small Ring Bicyclo[n...

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