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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

Codice CAS
77-73-6
Sinonimi
Cyclopentadiene dimer
3a,4,7,7a-Tetrahydro-4,7-methanoindene

Dimensioni Prezzo ($) Quantità Disponibilità
500ml 22,60
2500ml 64,10
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Dicyclopentadiene, 90+%, stab. with 4-tert-butylcatechol

MDL
MFCD00078246
EINECS
201-052-9

Proprietà chimiche

Formula
C10H12
Peso formula
132.21
Punto di ebollizione
171-173°
Punto di infiammabilità
26°(78°F)
Densità
0.982
Indice di rifrazione
1.5100
Solubilità
Immiscible with water.

Applicazioni

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.

Note

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.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H302-H332-H315-H319-H335

Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,2739
Beilstein
1904092
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2902.19
TSCA
Yes
RTECS
PC1050000

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