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2,5-Norbornadiene, 97%, stab with 250 ppm BHT
2,5-Norbornadiene, 97%, stab with 250 ppm BHT
2,5-Norbornadiene, 97%, stab with 250 ppm BHT
Thermo Scientific Chemicals

2,5-Norbornadiene, 97%, stab with 250 ppm BHT

CAS: 121-46-0 | C7H8 | 92.14 g/mol
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Quantity:
25 mL
100 mL
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Catalog number L13935.AC
also known as L13935-AC
Price (USD)
58.70
Each
Quantity:
25 mL
Request bulk or custom format
Price (USD)
58.70
Each
Chemical Identifiers
CAS121-46-0
IUPAC Namebicyclo[2.2.1]hepta-2,5-diene
Molecular FormulaC7H8
InChI KeySJYNFBVQFBRSIB-UHFFFAOYSA-N
SMILESC1C2C=CC1C=C2
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SpecificationsSpecification SheetSpecification Sheet
Assay (GC)≥96.0% (non-U.S. sourced material)
CommentMaterial sourced in the U.S. and in other countries
FormLiquid
Assay from Supplier's CofA≥96.0% (U.S. sourced material)
Refractive Index1.4685-1.4735 @ 20°C (non-U.S. sourced material)
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2,5-Norbornadiene is used as an intermediate in prostaglandin synthesis and shows anti-ethylene effect on plants. It acts as a starting material for the synthesis of diamantane and as an acetylene transfer agent for instance, in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. It is also a useful dienophile in Diels-Alder reactions.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
2,5-Norbornadiene is used as an intermediate in prostaglandin synthesis and shows anti-ethylene effect on plants. It acts as a starting material for the synthesis of diamantane and as an acetylene transfer agent for instance, in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. It is also a useful dienophile in Diels-Alder reactions.

Solubility
Immiscible with water.

Notes
Incompatible with strong oxidizing agents, strong acids and strong bases.
RUO – Research Use Only

General References:

  1. Bidentate π -ligand.
  2. The 2,4-pentanedionatorhodium complex: J. Chem. Soc. (A), 2334 (1971) has been used in the preparation of a chiral BINAP catalyst for homogeneous asymmetric hydrogenation: Org. Synth. Coll., 8, 420 (1993); see also (R)-(+)-2,2'-Bis(diphenyl phosphino)-1,1'-binaphthyl , B23785.
  3. Cycloaddition with Tetraphenyl cyclopentadienone, A12756, is followed by retro-Diels-Alder reaction with loss of cyclopentadiene to give 1,2,3,4-tetraphenylbenzene: J. Chem. Soc., 473 (1960).
  4. Similarly, pyrolysis of the adduct formed by 1,3-dipolar cycloaddition of acrylonitrile oxide provides a high-yield route to 3-vinylisoxazole: J. Chem. Soc., Chem. Commun., 2661 (1994).
  5. Aida, F.; Sone, H.; Ogawa, R.; Hamaoka, T.; Shimizu, I. Palladium-catalyzed 5-exo-Selective Reductive Mizoroki-Heck Reaction of Aryl Chlorides with 2,5-Norbornadiene. Chem. Lett.2015,44 (5), 715-717.
  6. Jia, H.; Shi, Y.; Ma, L.; Wang, Y.; Zang, Y.; Peng, J. Asymmetric polymerisation of substituted phenylacetylene using chiral Rh(2,5-norbornadiene)(L-proline) catalyst. Chem. Pap. 2015, 69 (5), 756-760.