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Merck
CN

792373

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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
329768330
MDL number:
MFCD00042123
Beilstein/REAXYS Number:
2251448
Assay:
95%
Form:
liquid

Key Documents

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InChI key

MNOONJNILVDLSW-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

95%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.4954

Quality Level

100

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

Related Categories

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

160.0 °F

flash_point_c

71.1 °C

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS3273V

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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
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2009)
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
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)

Related Content

Hu Group – Prof. Product Portal

Prof. Jinbo Hu's lab focuses on developing new fluorination reagents and reactions, including difluoromethylation and monofluoromethylation.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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