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A13643 Dicyclopentadiene, 90+%, stab. with 4-tert-butylcatechol

CAS Number
77-73-6
Synonyms
Cyclopentadiene dimer
3a,4,7,7a-Tetrahydro-4,7-methanoindene

Stock No. Size Price ($) Quantity Availability
A13643-AP 500ml 23.80
A13643-0F 2500ml 66.70
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Dicyclopentadiene, 90+%, stab. with 4-tert-butylcatechol

MDL
MFCD00078246
EINECS
201-052-9

Chemical Properties

Formula
C10H12
Formula Weight
132.21
Boiling Point
171-173°
Flash Point
26°(78°F)
Density
0.982
Refractive Index
1.5100
Storage & Sensitivity
Ambient temperatures.
Solubility
Immiscible with water.

Applications

Dicyclopentadiene is used in resins, particularly unsaturated polyester resins. It plays a major role in inks, adhesives and paints. It is also used as a monomer in polymerization reactions. It is a precursor for the preparation of endo-tetrahydrodicyclopentadiene, which reacts with aluminum chloride at higher temperature to give adamantine. It undergoes a retro-Diels-Alder reaction to yield cyclopentadiene, which acts as ligand in inorganic chemistry.

Notes

Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, strong acids and strong bases.

Literature References

Source, on heating, of monomeric cyclopentadiene. For details, see: Org. Synth. Coll., 7, 339 (1990).

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).

The cyclopentadienyl anion reacts with carbonyl compounds with the formation of fulvenes. For example using KOH and 18-crown-6, see: Synthesis, 799 (1980).

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).

Wang, L.; Ma, Y.; Qing, S.; Gao, Z.; Eli, W.; Wang, T. Magnetically Separable Fe3O4 Supported Co-Rh Bimetallic Catalysts for Dicyclopentadiene Hydroformylation to Value-Added Fine Chemicals. Energy Environ. Focus 2015, 4 (4), 334-339.

Autenrieth, B.; Jeong, H.; Forrest, W. P.; Axtell, J. C.; Ota, A.; Lehr, T.; Buchmeiser, M. R.; Schrock, R. R. Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of endo-Dicyclopentadiene by Molybdenum and Tungsten Catalysts. Macromolecules 2015, 48 (8), 2480-2492.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H302-H315-H319-H330-H335-H336-H373

Flammable liquid and vapour. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. Fatal if inhaled. May cause respiratory irritation. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P284-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P314-P330-P332+P313-P337+P313-P363-P370+P378q-P50

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Get medical advice/attention if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam

Other References

Merck
14,2739
Beilstein
1904092
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2902.19
TSCA
Yes
RTECS
PC1050000

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