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12108

Sigma-Aldrich

(±)-cis-Bicyclo[3.2.0]hept-2-en-6-one

≥98.0%

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About This Item

Empirical Formula (Hill Notation):
C7H8O
CAS Number:
13173-09-6
Molecular Weight:
108.14
MDL number:
MFCD06798168
UNSPSC Code:
12352100
PubChem Substance ID:
329749621
NACRES:
NA.22

Quality Level

100

assay

≥98.0% (GC)
≥98.0%

refractive index

n20/D 1.4820 (lit.)
n20/D 1.483

bp

158-160 °C (lit.)

density

1.025 g/mL at 25 °C (lit.)

SMILES string

O=C1C[C@@H]2C=CC[C@H]12

InChI

1S/C7H8O/c8-7-4-5-2-1-3-6(5)7/h1-2,5-6H,3-4H2/t5-,6-/m0/s1

InChI key

LNLLHUHPGPKRBM-WDSKDSINSA-N

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General description

(±)-cis-bicyclo(3.2.0)hept-2-en-6-one undergoes preparative scale Baeyer–Villiger biooxidation at high concentration using recombinant Escherichia coli biocatalyst and adsorbent resin (in situ substrate feeding and product removal)[1].

Application

(±)-(1S,5R)-cis-bicyclo(3.2.0)hept-2-en-6-one may be used:
  • to study enantioselective Baeyer–Villiger oxidation of (±)-cis-bicyclo(3.2.0)hept-2-en-6-one with H2O2 mediated by Co(Salen) catalyst in water with surfactants[2]
  • to investigate the extremophile enzymes (monooxygenase and hydrolases) in microorganisms isolated from deep-water petroleum reservoir and at high temperatures using fluorogenic assays and multibioreactions[3]
  • in the preparation of series of chalcone derivatives via reacton with arylaldehydes[4]

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH8616
BCBP5315V

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Asymmetric Baeyer-Villiger oxidation with Co (Salen) and H2O2 in water: striking supramolecular micelles effect on catalysis.
Bianchini G, et al.
Green Chemistry, 11(10), 1517-1520 (2009)
Iris Hilker et al.
Nature protocols, 3(3), 546-554 (2008-03-08)
An efficient biocatalytic process based on the use of adsorbent resin (in situ substrate feeding and product removal) makes experiments at high substrate concentration possible by overcoming limitations due to substrate and product inhibition. This process was successfully applied to
Synthesis and Characterization of New Chalcone Derivatives from cis-Bicyclo [3.2. 0] hept-2-en-6-one
Ceylan M and Findik E.
Synthetic Communications, 39(6), 1049-1054 (2009)
Kathleen Balke et al.
Chembiochem : a European journal of chemical biology, 18(16), 1627-1638 (2017-05-16)
Baeyer-Villiger monooxygenase (BVMO)-mediated regiodivergent conversions of asymmetric ketones can lead to the formation of "normal" or "abnormal" lactones. In a previous study, we were able to change the regioselectivity of a BVMO by mutation of the active-site residues to smaller
Georgiana F da Cruz et al.
Applied microbiology and biotechnology, 87(1), 319-329 (2010-03-06)
Microbial oxidation potentials of extremophiles recovered from Pampo Sul oil field, Campos Basin, Brazil, in pure culture or in consortia, were investigated using high-throughput screening (HTS) and multibioreactions. Camphor (1), cis-jasmone (2), 2-methyl-cyclohexanone (3), 1,2-epoxyoctane (4), phenylethyl acetate (5), phenylethyl
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Articles

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

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