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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/REAXYS Number:
1860145
EC Number:
222-458-2
MDL number:
MFCD00001294
UNSPSC Code:
12352100
PubChem Substance ID:
24847671
NACRES:
NA.22

vapor density

5 (vs air)

Quality Level

100

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.

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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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)

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