2-Cyclopenten-1-one Chemical Properties

Boiling point:

64-65 °C19 mm Hg(lit.)

Density 

0.98 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.481(lit.)

Flash point:

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

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)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

10-37-36/37/38-22

Safety Statements 

16-36-36/37/39

RIDADR 

UN 1224 3/PG 3

WGK Germany 

3

F 

8

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

29142990

MSDS

• Language:English Provider:2-Cyclopenten-1-one
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Cyclopenten-1-one Usage And Synthesis

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 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.

2-Cyclopenten-1-one(930-30-3)Related Product Information

• Cyclopentene
• Jasmone
• PHORBOL 12-MYRISTATE 13-ACETATE
• 3-methylcyclopent-2-en-1-one
• AMYL CYCLOPENTENONE,2-Pentyl-2-cyclopentenone
• PROSTAGLANDIN B1
• 2-HYDROXY-3-METHYL-2-CYCLOPENTENONE,3-METHYL-2-HYDROXY-2-CYCLOPENTENONE
• 2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE
• 3-Ethyl-2-hydroxy-2-cyclopenten-1-one
• 3-METHYL-2-PENTYL-2-CYCLOPENTENONE,2-Amyl-3-methyl-2-cyclopentenone,2-Pentyl-3-methyl-2-cyclopentenone
• 2-Methyl-2-cyclopentenone
• 4-CYCLOPENTENE-1,3-DIONE
• 2-HEXYL-2-CYCLOPENTENONE,2-n-Hexyl-2-cyclopentenone
• 2-Methyl-5-oxocyclopent-1-enyl propionate
• DIHYDRO ISOJASMONE
• 2-HYDROXY-3-METHYL-2-CYCLOPENTENONE
• Dichloro-1,2-dithiacyclopentenone
• Cyclopentanone