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5453-80-5 - 5-Norbornene-2-carboxaldehyde, endo + exo, 95% - Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde - B24973 - Alfa Aesar

B24973 5-Norbornene-2-carboxaldehyde, endo + exo, 95%

CAS Number
5453-80-5
Synonyms
Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde

Size Price ($) Quantity Availability
25g 46.80
100g 142.00
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5-Norbornene-2-carboxaldehyde, endo + exo, 95%

MDL
MFCD00167568
EINECS
226-698-9

Chemical Properties

Formula
C8H10O
Formula Weight
122.17
Boiling Point
68-70°/12mm
Flash Point
50°(122°F)
Density
1.032
Refractive Index
1.4910
Solubility
Not miscible in water.

Applications

5-Norbornene-2-carboxaldehyde was used in transition metal-catalyzed synthesis of norbornene-derived homopolymers having pendent t-Boc-protected quinizarin moieties for patterned fluorescence images. It acts as Diels-Alder adduct of acrolein and cyclopentadiene. It can be used as protected form of acrolein, from which the double bond may be liberated by cycloreversion, e.g. in a useful synthesis of 2-vinylimidazole.

Notes

Store away from air and oxidizing agents. Airsensitive. Store under dry inert gas.

Literature References

Jimmy Yoo; Jae-Hyoung Lee; Iwhan Cho; Kwang-Duk Ahn; Jong-Man Kim. The first synthesis of a transition metal-catalyzed homopolymer having pendentt-boc-protected quinizarin for patterned fluorescence images. Macromolecular Research.2003, 11, 69-72.

Diels-Alder adduct of acrolein and cyclopentadiene. Can be used as protected form of acrolein, from which the double bond may be liberated by cycloreversion, e.g. in a useful synthesis of 2-vinylimidazole: Angew. Chem. Int. Ed., 22, 560 (1983):

Aldol condensation with formaldehyde, followed by crossed Cannizzaro reduction, gives norbornene-2,2-dimethanol, from can be thermolyzed to vinyl-1,1-dimethanol: Tetrahedron Lett., 3775 (1975). For a review of cycloreversion reactions in organic synthesis, see: Synthesis, 121 (1985).

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H303

Flammable liquid and vapour. May be harmful if swallowed.

Precautionary Statements: P261

Avoid breathing dust/fume/gas/mist/vapours/spray.

Other References

Beilstein
1363813
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2912.29
TSCA
Yes

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