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454338

Sigma-Aldrich

Dicyclopentadiene

contains BHT as stabilizer

Synonym(s):

4,7-Methano-3a,4,7,7a-tetrahydroindene, Cyclopentadiene dimer, DCPD

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About This Item

Empirical Formula (Hill Notation):
C10H12
CAS Number:
77-73-6
Molecular Weight:
132.20
Beilstein:
1904092
EC Number:
201-052-9
MDL number:
MFCD00078246
UNSPSC Code:
12352100
PubChem Substance ID:
24868570
NACRES:
NA.22

contains

BHT as stabilizer

Quality Level

200

bp

170 °C (lit.)

mp

33 °C (lit.)

density

0.986 g/mL at 25 °C (lit.)

SMILES string

C1C=CC2C3CC(C=C3)C12

InChI

1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2/t7-,8+,9?,10?/m0/s1

InChI key

HECLRDQVFMWTQS-AFWXGSBKSA-N

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General description

Dicyclopentadiene(DCPD) is a dimer of cyclopentadiene composed of two unsaturated double bonds(one in the norbornene ring and one in the cyclopentene ring). DCPT is used inpolymers by itself and with other hydrocarbons. It is also employed in pharmaceuticals,elastomers, polycarbonates, and polyester resins.

Application

Dicyclopentadiene may be used:
  • In the preparation of CF/p-DCPD ((carbon fiber/ poly-dicyclopentadiene) composites by VARTM (vacuum-assisted resin transfer molding) process.
  • In the preparation of η5-cyclopentadienyltris(dimethylamido)zirconium catalyst.
  • In the synthesis of cellulose – maleic anhydride– dicyclopentadiene copolymer matrix by free radical polymerization.

Features and Benefits

DCPD has the following advantages over orthophthalic andisophthalic polyesters:
  • Low shrinkage
  • Cost-effective
  • Reduced emissions of styrene
  • Fast curing in thin layers.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sebastijan Kovačič et al.
ACS applied materials & interfaces, 6(21), 19075-19081 (2014-10-22)
Zinc(II) oxide nanoparticles were used for the stabilization of dicyclopentadiene (DCPD)-water-based high internal phase emulsions (HIPEs), which were subsequently cured using ring-opening metathesis polymerization (ROMP). The morphology of the resulting ZnO-pDCPD nanocomposite foams was investigated in correlation to the nanoparticle
Frontal ring-opening metathesis polymerization of dicyclopentadiene.
Mariani A, et al.
Macromolecules, 34(19), 6539-6541 (2001)
Morphological and mechanical evaluation of hybrid organic-inorganic thermoset copolymers of dicyclopentadiene and mono-or tris (norbornenyl)-substituted polyhedral oligomeric silsesquioxanes.
Constable GS, et al.
Macromolecules, 37(4), 1276-1282 (2004)
Anna Kozłowska et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(43), 14120-14125 (2014-09-11)
Cyclic Ru-phenolates were synthesized, and these compounds were used as olefin metathesis catalysts. Investigation of their catalytic activity pointed out that, after activation with chemical agents, these catalysts promote ring-closing metathesis (RCM), enyne and cross-metathesis (CM) reactions, including butenolysis, with
Andre H St Amant et al.
Journal of the American Chemical Society, 141(34), 13619-13624 (2019-08-08)
Herein, we report the development of a scalable and synthetically robust building block based on norbornadiene (NBD) that can be broadly incorporated into a variety of macromolecular architectures using traditional living polymerization techniques. By taking advantage of a selective and
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