Skip to Content
Merck
All Photos(1)

Documents

466433

Sigma-Aldrich

1-Acetyl-1-cyclopentene

97%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C5H7COCH3
CAS Number:
16112-10-0
Molecular Weight:
110.15
MDL number:
MFCD00799464
UNSPSC Code:
12352100
PubChem Substance ID:
24870347
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.483 (lit.)

bp

70 °C/20 mmHg (lit.)

density

0.955 g/mL at 25 °C (lit.)

SMILES string

CC(=O)C1=CCCC1

InChI

1S/C7H10O/c1-6(8)7-4-2-3-5-7/h4H,2-3,5H2,1H3

InChI key

SLNPSLWTEUJUGY-UHFFFAOYSA-N

General description

1-Acetyl-1-cyclopentene is a cyclic alkene. Its lithium enolate undergoes Brook rearrangement-mediated [3+4] annulation with 3-alkyl-3-haloacryloylsilanes to afford tricyclo[5.3.0.01,4]decenone derivatives. Asymmetric oxidative Heck reaction of 1-acetyl-1-cyclopentene in the presence of a Pd-ligand has been reported.

Application

1-Acetyl-1-cyclopentene may be used in the preparation of the following allenylcycloalkanes:
  • 1-vinylidenyl-2-[4-(trimethylsilyl)-3-butynyl]-cyclopentane
  • 1-vinylidenyl-2-(3-butynyl)-cyclopentane

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

138.2 °F - closed cup

Flash Point(C)

59 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Facile Construction of a Tricyclo [5.3. 0.01, 4] decenone Ring System by the Brook Rearrangement-Mediated [3+4] Annulation.
Takeda K and Ohtani Y.
Organic Letters, 1(4), 677-680 (1999)
B Green et al.
Steroids, 59(8), 479-484 (1994-08-01)
The addition of diphenylnitrilimine and C-o-chlorodiphenylnitrilimine to 3 beta-hydroxyandrost-5,16-diene (3b) produced a 1/1 ratio of regioisomeric, 1,3-diaryl-2-pyrazolines (6a, 7a and 6b, 7b), whereas the addition of N-o-chlorodiphenylnitrilimine gave a 5/1 ratio in favor of the [17 alpha, 16 alpha-d] regioisomer
An intramolecular allenic [2+ 2+ 1] cycloaddition.
Brummond KM, et al.
The Journal of Organic Chemistry, 63(9), 6535-6545 (1998)
Kyung Soo Yoo et al.
The Journal of organic chemistry, 75(1), 95-101 (2009-12-04)
Chiral dimeric tridentate NHC-amidate-alkoxide palladium(II) complexes, 3a and 3b, effected oxidative boron Heck-type reactions of aryl boronic acids with both acyclic and cyclic alkenes at room temperature to afford the corresponding coupling products with high enantioselectivities. The high degree of

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service