tricyclo[5.2.1.0^{2,6}]deca-3,8-diene

• ChemBase ID: 108886
• Molecular Formular: C10H12
• Molecular Mass: 132.20228
• Monoisotopic Mass: 132.09390038
• SMILES: C1C=CC2C3CC(C=C3)C12
• Canonical SMILES: C1=CC2C(C1)C1C=CC2C1
• InChI: InChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2
• InChIKey: HECLRDQVFMWTQS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tricyclo[5.2.1.0^{2,6}]deca-3,8-diene; tricyclo[5.2.1.0^2,^6]deca-3,8-diene
• IUPAC Traditional name: dicyclopentadiene
• Synonyms: DICYCLOPENTADIENE; 1,3-Dicyclopentadiene; Dicyclopentadiene; Cyclopentadiene dimer; 3a,4,7,7a-Tetrahydro-4,7-methanoindene; 二环戊二烯

Database IDs

• CAS Number: 77-73-6
• EC Number: 247-724-5; 201-052-9
• MDL Number: MFCD00078246
• Beilstein Number: 1904092
• Merck Index: 142739
• PubChem SID: 162088921
• PubChem CID: 6492
• Chemspider ID: 6247
• KEGG ID: C14411
• MeSH Name: Dicyclopentadiene
• Wikipedia Title: Dicyclopentadiene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.1641932
• LogD (pH = 7.4): 2.1641932
• Log P: 2.1641932
• Molar Refractivity: 44.4292 cm^3
• Polarizability: 16.519753 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Melting Point: 32.5 °C; 6°C
• Boiling Point: 170 °C; 170°C; 171-173°C
• Flash Point: 26°C(78°F); 32 °C
• Density: 0.977 g/ml; 0.98 g/cm^3; 0.982
• Refractive Index: 1.5100

Safety Information

• RTECS: PC1050000
• European Hazard Symbols: Flammable (F); Nature polluting (N); X
• UN Number: UN 2048; UN2048
• Hazard Class: 3
• Packing Group: III
• Risk Statements: 11-20/22-36/37/38-51/53; R:11-20/22-36/37/38-51/53
• Safety Statements: 36/37-61; S:61-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07; GHS09
• NFPA704:
  

  3

  1

  1
• GHS Hazard statements: H225-H302-H332-H315-H319-H335-H411
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A

Product Information

• Purity: 90+%, stab. with 4-tert-butylcatechol; typically 95%, stab.

DETAILS

MP Biomedicals - 05209108

MP Biomedicals Rare Chemical collection

REFERENCES

• Source, on heating, of monomeric cyclopentadiene. For details, see: Org. Synth. Coll., 7, 339 (1990).
• The cyclopentadienyl anion reacts with carbonyl compounds with the formation of fulvenes. For example using KOH and 18-crown-6, see: Synthesis, 799 (1980).
• Diels-Alder reaction with 1,4-benzoquinones and subsequent retro Diels-Alder with elimination of cyclopentadiene have been used in synthesis of 2-cyclohexene-1,4-diones: J. Chem. Soc. (C), 124 (1969); Org. Synth. Coll., 9, 186 (1998). For an enantioselective, catalytic Diels-Alder reaction, see: Org. Synth. Coll., 9, 67 (1998).
• Readily deprotonated by strong bases to give the 6πAlpha/Delectron cyclopentadienyl anion, which forms stable complexes with many transition metals. Conversion to ferrocene by two alternative procedures: Org. Synth. Coll., 4, 473 (1963), or using crown-ether catalysis: Angew. Chem. Int. Ed., 18, 792 (1979). Preparation of ruthenocene: Org. Synth. Coll., 5, 1001 (1973).
• For a review of methods for the synthesis of a wide variety of 1,3-bifunctionalized cyclopentanes and cyclopentenes from cyclopentadiene, see: Angew. Chem. Int. Ed., 21, 480 (1982).