bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

• ChemBase ID: 288894
• Molecular Formular: C8H10O
• Molecular Mass: 122.1644
• Monoisotopic Mass: 122.07316494
• SMILES: O=CC1CC2C=CC1C2
• Canonical SMILES: O=CC1CC2CC1C=C2
• InChI: InChI=1S/C8H10O/c9-5-8-4-6-1-2-7(8)3-6/h1-2,5-8H,3-4H2
• InChIKey: AJIBZRIAUXVGQJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• IUPAC Traditional name: bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• Synonyms: 5-Norbornene-2-carboxaldehyde; Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde; 5-Norbornene-2-carboxaldehyde, endo + exo; 5-降冰片烯-2-甲醛, endo + exo

Database IDs

• CAS Number: 5453-80-5
• EC Number: 226-698-9
• MDL Number: MFCD00167568
• Beilstein Number: 1363813
• PubChem SID: 180674425
• PubChem CID: 95117

CALCULATED PROPERTIES

• Acid pKa: 18.720486
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.0353622
• LogD (pH = 7.4): 1.0353622
• Log P: 1.0353622
• Molar Refractivity: 36.7311 cm^3
• Polarizability: 13.837097 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 68-70°C/12mm
• Flash Point: 50°C(122°F)
• Density: 1.032
• Refractive Index: 1.4910

Safety Information

• UN Number: UN1989
• Hazard Class: 3
• Packing Group: III
• Risk Statements: 10
• TSCA Listed: 是
• GHS Pictograms: GHS02
• GHS Hazard statements: H226-H303
• GHS Precautionary statements: P261

Product Information

• Purity: 95%; 95+%; 98%

REFERENCES

• 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).