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121-46-0 - 2,5-Norbornadiene, 97%, stab with 250 ppm BHT - Bicyclo[2.2.1]hepta-2,5-diene - L13935 - Alfa Aesar

L13935 2,5-Norbornadiene, 97%, stab with 250 ppm BHT

CAS Number
121-46-0
Synonyms
Bicyclo[2.2.1]hepta-2,5-diene

Size Price ($) Quantity Availability
25ml 34.30
100ml 78.07
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2,5-Norbornadiene, 97%, stab with 250 ppm BHT

MDL
MFCD00082301
EINECS
204-472-0

Chemical Properties

Formula
C7H8
Formula Weight
92.14
Melting point
-20°
Boiling Point
88-90°
Flash Point
-11°(12°F)
Density
0.906
Refractive Index
1.4700
Solubility
Immiscible with water.

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.

Notes

Incompatible with strong oxidizing agents, strong acids and strong bases.

Literature References

Bidentate π -ligand.

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(diphenyl­phosphino)-1,1'-binaphthyl­, B23785.

Cycloaddition with Tetraphenyl­cyclopentadienone, A12756, is followed by retro-Diels-Alder reaction with loss of cyclopentadiene to give 1,2,3,4-tetraphenylbenzene: J. Chem. Soc., 473 (1960).

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).

/n

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.

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H303

Highly flammable liquid and vapour. May be harmful if swallowed.

Precautionary Statements: P210-P280-P240-P241-P233-P242-P303+P361+P353-P312-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Call a POISON CENTER or doctor/physician if you feel unwell. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
506224
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2902.19
TSCA
Yes
RTECS
RB6535000

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