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77-73-6 - Dicyclopentadiene, 90+%, stab. with 4-tert-butylcatechol - Cyclopentadiene dimer - 3a,4,7,7a-Tetrahydro-4,7-methanoindene - A13643 - Alfa Aesar

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

CAS-Nummer
77-73-6
Synonyme
Cyclopentadiene dimer
3a,4,7,7a-Tetrahydro-4,7-methanoindene

Größe Preis ($) Menge Verfügbarkeit
500ml 22,45
2500ml 63,76
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Dicyclopentadiene, 90+%, stab. with 4-tert-butylcatechol

MDL
MFCD00078246
EINECS
201-052-9

Chemische Eigenschaften

Formel
C10H12
Molmasse
132.21
Siedepunkt
171-173°
Flammpunkt
26°(78°F)
Dichte
0.982
Brechungsindex
1.5100
Löslichkeit
Immiscible with water.

Anwendungen

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.

Bemerkungen

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.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H225-H302-H332-H315-H319-H335-H411

Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Toxic to aquatic life with long lasting effects.

Sicherheitshinweise: P210-P261-P273-P280-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,2739
Beilstein
1904092
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2902.19
TSCA
Yes
RTECS
PC1050000

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