5-Norbornene-2-carboxaldehyde, endo + exo, 95%, Thermo Scientific Chemicals

Name: 5-Norbornene-2-carboxaldehyde, endo + exo, 95%, Thermo Scientific Chemicals
SKU: B24973.22

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Catalog number B24973.22

also known as B24973-22

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Chemical Identifiers

CAS5453-80-5

IUPAC Namebicyclo[2.2.1]hept-5-ene-2-carbaldehyde

Molecular FormulaC8H10O

InChI KeyAJIBZRIAUXVGQJ-UHFFFAOYNA-N

SMILESO=CC1CC2CC1C=C2

Specifications

Specification Sheet

Free acid (titration)≤2.0%

Refractive Index1.4870-1.4970 @ 20?C

Appearance (Color)Clear colorless to yellow

FormLiquid

Assay (GC)≥94.0% (sum of endo + exo isomers)

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.

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
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.

Solubility
Not miscible in water.

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

RUO – Research Use Only

General 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).