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344508

Sigma-Aldrich

Cyclopentene

96%

Synonym(s):

2,2-Dimethylacetyl chloride

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About This Item

Empirical Formula (Hill Notation):
C5H8
CAS Number:
142-29-0
Molecular Weight:
68.12
Beilstein/REAXYS Number:
635707
EC Number:
205-532-9
MDL number:
MFCD00001394
UNSPSC Code:
12352100
PubChem Substance ID:
24861258
NACRES:
NA.22

vapor pressure

20.89 psi ( 55 °C)
6.11 psi ( 20 °C)

assay

96%

form

liquid

autoignition temp.

743 °F

refractive index

n20/D 1.421 (lit.)

bp

44-46 °C (lit.)

mp

−135 °C (lit.)

solubility

water: soluble 0.535 g/L at 25 °C

density

0.771 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C1CC=CC1

InChI

1S/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2

InChI key

LPIQUOYDBNQMRZ-UHFFFAOYSA-N

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General description

Cyclopentene is a cyclo-olefin. Neopentyl phosphine ligand catalyzed Heck coupling of cyclopentene has been reported. Mechanism of reaction of ground state oxygen atom with cyclopentene has been investigated. Homopolymerization of cyclopentene has been reported. Photocatalytic oxidation of cyclopentene over various titanium(IV) oxide catalyst has been reported.

Application

Cyclopentene was used to investigate the [2+2] cycloaddition of diamond (001) surfaces with alkene.

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Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Asp. Tox. 1 - Flam. Liq. 2 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

-29.9 °F - closed cup

flash_point_c

-34.4 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Stereospecific homopolymerization of cyclopentene.
Natta G, et al.
Angewandte Chemie (International Edition in English), 3(11), 723-729 (1964)
Hongmei Zhao et al.
Journal of molecular graphics & modelling, 51, 184-192 (2014-06-18)
The reaction mechanism of the ground state oxygen atom O((3)P) with cyclopentene is investigated theoretically. The triplet and singlet potential energy surfaces are calculated at the CCSD(T)//MP2/6-311G(d,p) level and the minimum energy crossing points (MECPs) between the two surfaces are
Cycloaddition chemistry at surfaces: reaction of alkenes with the diamond (001)-2? 1 surface.
Hovis JS, et al.
Journal of the American Chemical Society, 122(4), 732-733 (2000)
Partial photocatalytic oxidation of cyclopentene over titanium (IV) oxide.
Kluson P, et al.
J. Mol. Catal. A: Chem., 242(1), 62-67 (2005)
Matthew G Lauer et al.
The Journal of organic chemistry, 79(22), 10837-10848 (2014-10-22)
The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of
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