bicyclo[2.2.1]hepta-2,5-diene

• ChemBase ID: 109248
• Molecular Formular: C7H8
• Molecular Mass: 92.13842
• Monoisotopic Mass: 92.06260026
• SMILES: C1C2C=CC1C=C2
• Canonical SMILES: C1=CC2CC1C=C2
• InChI: InChI=1S/C7H8/c1-2-7-4-3-6(1)5-7/h1-4,6-7H,5H2
• InChIKey: SJYNFBVQFBRSIB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bicyclo[2.2.1]hepta-2,5-diene
• IUPAC Traditional name: norbornadiene
• Synonyms: BICYCLO(2.2.1)HEPTA-2,5-DIENE; quadricyclo[2.2.1.02,6.03.5]heptane; tetracyclo[2.2.1.02,6.03,5]heptane; Quadricyclane; bicyclo[2.2.1]hepta-2,5-diene; Bicyclo[2.2.1]hepta-2,5-diene; 2,5-Norbornadiene; 2,5-Norbornadiene; Norbornadiene; 2,5-降冰片二烯

Database IDs

• CAS Number: 278-06-8; 121-46-0
• EC Number: 204-472-0
• MDL Number: MFCD00082301
• Beilstein Number: 506224
• PubChem SID: 162095001
• PubChem CID: 8473
• Wikipedia Title: Quadricyclane; Norbornadiene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.6093123
• LogD (pH = 7.4): 1.6093123
• Log P: 1.6093123
• Molar Refractivity: 32.5332 cm^3
• Polarizability: 11.724419 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water
• Melting Point: -19°C; -20°C; -44°C
• Boiling Point: 108°C (at 987 hPa); 88-90°C; 89°C
• Flash Point: -11°C(12°F)
• Density: 0.906; 0.906 g/cm3; 0.982 g/cm^3
• Refractive Index: 1.4700
• Hydrophobicity(logP): 2.141

Safety Information

• RTECS: RB6535000
• European Hazard Symbols: Flammable (F)
• UN Number: UN2251
• Hazard Class: 3
• Packing Group: II
• Risk Statements: 11; R:10; R11; R11 R23
• Safety Statements: 33; S:9-16-29; S16 S29 S33 S45; S9 S16 S29 S33
• TSCA Listed: 是
• GHS Pictograms: GHS02
• GHS Hazard statements: H225
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A

Product Information

• Purity: 95%; 97%; 97%, stab with 250 ppm BHT

DETAILS

MP Biomedicals - 05210335

MP Biomedicals Rare Chemical collection

REFERENCES

• 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).
• Bidentate π -ligand.