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53896

Sigma-Aldrich

3-Phenylcyclobutanone

≥95.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C10H10O
CAS Number:
52784-31-3
Molecular Weight:
146.19
MDL number:
MFCD04038993
UNSPSC Code:
12352100
PubChem Substance ID:
329758016

Assay

≥95.0% (HPLC)

form

solid

refractive index

n20/D 1.544

SMILES string

O=C1CC(C1)c2ccccc2

InChI

1S/C10H10O/c11-10-6-9(7-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2

InChI key

BVQSFCUGCAZOJQ-UHFFFAOYSA-N

General description

Cationic Co(III)(salen) complex catalyzes the asymmetric Baeyer–Villiger reaction of 3-phenylcyclobutanone. Chiral N1,N10-ethylene-bridged flavinium salts catalyzes the H2O2 oxidation of 3-phenylcyclobutanone to afford the corresponding lactones. 3-Phenylcyclobutanone can be synthesized from 2,2-dichloro3-phenylcyclobutenone.

Application

3-Phenylcyclobutanone may be used in synthesizing γ-butyrolactones and 2,4-bis(dimethylaminomethyl)-3-phenylcyclobutane.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Cationic Co (III)(salen)-catalyzed enantioselective Baeyer?Villiger oxidation of 3-arylcyclobutanones using hydrogen peroxide as a terminal oxidant
Uchida T and Katsuki T
Tetrahedron Letters, 42.39, 6911-6914 (2001)
N1, N10-Ethylene-bridged flavinium salts derived from L-valinol: synthesis and catalytic activity in H2O2 oxidations
Zurek J, et al.
Tetrahedron Letters, 51.7 , 1083-1086 (2010)
Phenylcyclobutane Amino Alcohols and Amino Ketones
Burger A and Ong HH
The Journal of Organic Chemistry, 29.9 , 2588-2592 (1964)
An enantioselective synthesis of 3, 4-disubstituted butyrolactones
Honda T and Kimura N
Journal of the Chemical Society. Chemical Communications, 1, 77-78 (1994)
Small-Ring Compounds. XI. Some New Cyclobutane, Cyclobutene and Cyclobutanone Derivatives Derived from the Adduct of Phenylacetylene with 1, 1-Difluoro-2, 2-dichloroethylene
Roberts JD, et al.
Journal of the American Chemical Society, 75.19, 4765-4768 (1953)

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