125512
Cyclopropyl phenyl ketone
97%
Synonym(s):
Benzoylcyclopropane
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About This Item
Linear Formula:
C6H5COC3H5
CAS Number:
Molecular Weight:
146.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
222-458-2
Beilstein/REAXYS Number:
1860145
MDL number:
Assay:
97%
InChI key
PJRHFTYXYCVOSJ-UHFFFAOYSA-N
InChI
1S/C10H10O/c11-10(9-6-7-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2
SMILES string
O=C(C1CC1)c2ccccc2
vapor density
5 (vs air)
assay
97%
Quality Level
bp
121-123 °C/15 mmHg (lit.)
mp
7-9 °C (lit.)
density
1.058 g/mL at 25 °C (lit.)
Related Categories
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
194.0 °F - closed cup
flash_point_c
90 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Regulatory Information
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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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