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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

Quality Level

100

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.[1] Chiral N1,N10-ethylene-bridged flavinium salts catalyzes the H2O2 oxidation of 3-phenylcyclobutanone to afford the corresponding lactones.[2] 3-Phenylcyclobutanone can be synthesized from 2,2-dichloro3-phenylcyclobutenone.[3]

Application

3-Phenylcyclobutanone may be used in synthesizing γ-butyrolactones[4] and 2,4-bis(dimethylaminomethyl)-3-phenylcyclobutane.[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD0934V
1345270

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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)
An enantioselective synthesis of 3, 4-disubstituted butyrolactones
Honda T and Kimura N
Journal of the Chemical Society. Chemical Communications, 1, 77-78 (1994)
Phenylcyclobutane Amino Alcohols and Amino Ketones
Burger A and Ong HH
The Journal of Organic Chemistry, 29.9 , 2588-2592 (1964)
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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