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792373

Sigma-Aldrich

2-Chloro-2,2-difluoroacetophenone

95%

Synonym(s):

2-Chloro-2,2-difluoro-1-phenylethanone, Chlorodifluoromethyl phenyl ketone, α-Chloro-α,α-difluoroacetophenone

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About This Item

Linear Formula:
C6H5COCF2Cl
CAS Number:
384-67-8
Molecular Weight:
190.57
Beilstein:
2251448
MDL number:
MFCD00042123
UNSPSC Code:
12352101
PubChem Substance ID:
329768330
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.4954
n20/D 1.497 (lit.)

bp

94-96 °C/35 mmHg (lit.)

density

1.293 g/mL at 25 °C (lit.)
1.3178 g/mL at 25 °C

functional group

chloro
fluoro
ketone
phenyl

SMILES string

FC(F)(Cl)C(=O)c1ccccc1

InChI

1S/C8H5ClF2O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5H

InChI key

MNOONJNILVDLSW-UHFFFAOYSA-N

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General description

2-Chloro-2,2-difluoroacetophenone is a difluorocarbene reagent, which is generally used in the synthesis of 2,2-difluoro enol silyl ethers, and gem -difluoromethene derived compounds.

Application

2-Chloro-2,2-difluoroacetophenone can be used:
  • As a reagent in the difluoromethylation of various phenols to yield aryl difluoromethyl ethers.
  • As a precursor in the Baylis-Hillman reaction of fluoroalkyl ketones to obtain chlorodifluoromethyl containing products.
  • As a substrate in the synthesis of propargyl alcohols using a novel ruthenium catalyst.

Reagent is an effective product for the synthesis of difluoromethylated phenols in the presence of mild base and aqueous solvent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

160.0 °F

Flash Point(C)

71.1 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS3273V

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Laijun Zhang et al.
The Journal of organic chemistry, 71(26), 9845-9848 (2006-12-16)
A novel and non-ODS-based (ODS = ozone-depleting substance) preparation of 2-chloro-2,2-difluoroacetophenone (1) was achieved in high yield by using 2,2,2-trifluoroacetophenone as the starting material. Compound 1 was found to act as a good difluorocarbene reagent, which readily reacts with a
Octahedral ruthenium complex with exclusive metal-centered chirality for highly effective asymmetric catalysis
Zheng Y, et al.
Journal of the American Chemical Society, 139(12), 4322-4325 (2017)
2-Chloro-2, 2-difluoroacetophenone: a non-ODS-based difluorocarbene precursor and its use in the difluoromethylation of phenol derivatives
Zhang L, et al.
The Journal of Organic Chemistry, 71(26), 9845-9848 (2006)
Study of Fluorocarbonyls for the Baylis- Hillman Reaction
Ram Reddy MV, et al.
The Journal of Organic Chemistry, 67(15), 5382-5385 (2002)
2-Chloro-2,2-difluoroacetophenone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2009)

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