| Identification | More | [Name]
2-Cyclopentenone | [CAS]
930-30-3 | [Synonyms]
2-CYCLOPENTEN-1-ONE
2-CYCLOPENTENE-1-ONE
2-CYCLOPENTENONE
CPEO
CYCLOPENT-2-ENONE
2_cyclopenten-1-0ne
2-cyclopenten-1-0ne
2-Cyclopentenone-1
3-Cyclopenten-2-one
Cyclopenten-3-one
Cyclopentenone
cyclopenten-2-one
2-Cyclopentenone, pure, 98%
Cyclopent-2-en-1-one 97%
1-Cyclopenten-3-one
2-Cyclopentenone, 98%, pure
Cyclopent-2-en-3-one | [EINECS(EC#)]
213-213-0 | [Molecular Formula]
C5H6O | [MDL Number]
MFCD00001401 | [Molecular Weight]
82.1 | [MOL File]
930-30-3.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [Boiling point ]
64-65 °C19 mm Hg(lit.)
| [density ]
0.98 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.481(lit.)
| [Fp ]
108 °F
| [storage temp. ]
2-8°C
| [solubility ]
soluble in Chloroform, Methanol | [form ]
Liquid | [color ]
Clear yellow | [Specific Gravity]
0.980 | [Water Solubility ]
almost insoluble | [Detection Methods]
GC | [BRN ]
1446054 | [InChI]
InChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2 | [InChIKey]
BZKFMUIJRXWWQK-UHFFFAOYSA-N | [SMILES]
C1(=O)CCC=C1 | [LogP]
-0.114 (est) | [CAS DataBase Reference]
930-30-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Cyclopenten-1-one(930-30-3) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R10:Flammable.
R37:Irritating to the respiratory system.
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 1224 3/PG 3
| [WGK Germany ]
3
| [F ]
8 | [Hazard Note ]
Irritant | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29142990 |
| Hazard Information | Back Directory | [Description]
2-Cyclopentenone contains two functional groups, a ketone and an alkene. It is a colourless liquid. 2-cyclopenten-1-one selectively induces the expression of the 70-kDa HSP (HSP70) in human cells through cycloheximide-sensitive activation of heat shock transcription factor 1 (HSF1). It is a natural product found in Perilla frutescens[1].
| [Chemical Properties]
clear yellow liquid | [Uses]
2-Cyclopenten-1-one(930-30-3) is a versatile electrophile employed in various addition reactions including conjugate addition of organocopper nucleophiles, Michael reaction with silyl enol ethers and siloxanes. It is also used in Diels-Alder cycloadditions and phosphoniosilylations.
| [Definition]
ChEBI: 2-cyclopenten-1-one is an enone that is cyclopentanone having a C=C double bond at position 2. It has a role as a Hsp70 inducer. It is an enone and an alicyclic ketone. | [Preparation]
2-Cyclopentenones can be synthesized in a number of ways. One of the routes involves elimination of α-bromo-cyclopentanone using lithium carbonate and Claisen condensation-decarboxylation-isomerization cascades of unsaturated diesters as shown below.
The acid-catalyzed dehydration of cyclopentanediols affords cyclopentenone.
As a functional group, the synthesis of 2-cyclopentenones is accomplished in a variety of other ways, including the Nazarov cyclization reaction from divinyl ketones, Saegusa–Ito oxidation from cyclopentanones, ring-closing metathesis from the corresponding dienes, oxidation of the corresponding cyclic allylic alcohols, and the Pauson–Khand reaction from alkenes, alkynes, and carbon monoxide.
en.wikipedia.org | [References]
[1] A Rossi, M G Santoro, G Elia. “2-Cyclopenten-1-one, a new inducer of heat shock protein 70 with antiviral activity.” The Journal of Biological Chemistry 271 50 (1996): 32192–6.
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