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125512

Sigma-Aldrich

Cyclopropyl phenyl ketone

97%

Synonym(s):

Benzoylcyclopropane

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About This Item

Linear Formula:
C6H5COC3H5
CAS Number:
3481-02-5
Molecular Weight:
146.19
Beilstein:
1860145
EC Number:
222-458-2
MDL number:
MFCD00001294
UNSPSC Code:
12352100
PubChem Substance ID:
24847671
NACRES:
NA.22

vapor density

5 (vs air)

Assay

97%

refractive index

n20/D 1.553 (lit.)

bp

121-123 °C/15 mmHg (lit.)

mp

7-9 °C (lit.)

density

1.058 g/mL at 25 °C (lit.)

SMILES string

O=C(C1CC1)c2ccccc2

InChI

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

InChI key

PJRHFTYXYCVOSJ-UHFFFAOYSA-N

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Application

Cyclopropyl phenyl ketone was used to prepare α-cyclopropylstyrene by the Wittig reaction in dimethyl sulfoxide. It was used as starting reagent during the (Z)-titanium enolate formation from cyclopropyl ketones via TiCl4-n-Bu4NI-induced ring opening reaction.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

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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Cyclopropyl substituent effects on acid-catalyzed hydration of alkenes. Correlation by σ+ parameters.
Oyama K and Tidwell TT.
Journal of the American Chemical Society, 98(4), 947-951 (1976)
Enolate formation from cyclopropyl ketones via iodide-induced ring opening and its use for stereoselective aldol reaction.
Han Z, et al.
Tetrahedron, 57(6), 987-995 (2001)
C Zimmermann et al.
Physical chemistry chemical physics : PCCP, 22(5), 2870-2877 (2020-01-09)
The two hydrogen bond solvation sites exhibited by the carbonyl group in acetophenone are influenced by alkylation of the methyl group in both the acetophenone and in the prototype solvent methanol, largely due to London dispersion forces. Phenyl docking and

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