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Sigma-Aldrich

4-Chlorobutyrophenone

technical grade

Synonym(s):

γ-Chlorobutyrophenone, 4-Chloro-1-phenyl-1-butanone

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About This Item

Linear Formula:
C6H5COCH2CH2CH2Cl
CAS Number:
Molecular Weight:
182.65
Beilstein:
878974
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

form

liquid

refractive index

n20/D 1.544 (lit.)

mp

19-20 °C (lit.)

density

1.137 g/mL at 25 °C (lit.)

SMILES string

ClCCCC(=O)c1ccccc1

InChI

1S/C10H11ClO/c11-8-4-7-10(12)9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

InChI key

GHEFQKHLHFXSBR-UHFFFAOYSA-N

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General description

4-Chlorobutyrophenone is a chloro ketone. Preparation of 4-chlorobutyrophenone is reported.

Application

4-Chlorobutyrophenone may be used in the preparation of silyl enol ether, Z-4-chloro-1-phenyl-1-trimethylsilyloxybut-1-ene. It may be used as starting material in the preparation of 8-arylimidazopyridines.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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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The Journal of Organic Chemistry, 52, 1863-1863 (1987)
William J Kerr et al.
Organic & biomolecular chemistry, 6(7), 1238-1243 (2008-03-26)
Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes(2)Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high
Neighboring group participation by carbonyl oxygen.
Pasto DJ and Serve MP.
Journal of the American Chemical Society, 87(7), 1515-1521 (1965)

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