Dicyclopentadiene

• Catalog No.: A13643
• CAS Number: 77-73-6
• M. F.: C10H12
• M. W.: 132.20228
• Purity: 90+%, stab. with 4-tert-butylcatechol

SYNONYMS

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

DATABASE IDS

• CAS Number: 77-73-6
• MDL Number: MFCD00078246
• Merck Index: 142739
• EC Number: 201-052-9
• Beilstein Number: 1904092

PROPERTIES

• Purity: 90+%, stab. with 4-tert-butylcatechol
• Boiling Point: 171-173°C
• Density: 0.982
• Flash Point: 26°C(78°F)
• Refractive Index: 1.5100
• GHS Hazard statements: H225-H302-H332-H315-H319-H335-H411
• European Hazard Symbols: X
• European Hazard Symbols: Flammable (F)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-20/22-36/37/38-51/53
• RTECS: PC1050000
• Safety Statements: 36/37-61
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2048
• Packing Group: III

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).