2-Cyclopenten-1-one Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

2-Cyclopenten-1-one Chemical Properties,Usage,Production

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.