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Sigma-Aldrich

Difluoromethyl 2-pyridyl sulfone

97% (HPLC)

Synonym(s):

2-[(Difluoromethyl)sulfonyl]pyridine, Hu Reagent, 2-(Difluoromethylsulfonyl)pyridine, 2-PySO2CF2H

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About This Item

Empirical Formula (Hill Notation):
C6H5F2NO2S
CAS Number:
1219454-89-3
Molecular Weight:
193.17
Beilstein/REAXYS Number:
20317604
MDL number:
MFCD17010193
UNSPSC Code:
12352101
PubChem Substance ID:
329765740
NACRES:
NA.22

assay

97% (HPLC)

form

solid

mp

44-49 °C

SMILES string

O=S(C1=CC=CC=N1)(C(F)F)=O

InChI

1S/C6H5F2NO2S/c7-6(8)12(10,11)5-3-1-2-4-9-5/h1-4,6H

InChI key

YRQNSTAWTLXCEZ-UHFFFAOYSA-N

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General description

Difluoromethyl 2-pyridyl sulfone (2-PySO2CF2H) is a reagent used in the gem-difluoroolefination of aldehydes and ketones. It is also used as a reagent in the nucleophilic difluoro(sulfonato)methylation of alcohols, N-sulfinyl imines, and halides.

Application

Reagent is used in the olefination of ketones and aldehydes to form gem-difluoro olefins under basic conditions. Product is also used as a crucial intermediate toward making 1,1-difluorinated alkyl chains for the alkylation of heterocycles.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Difluoromethyl 2-pyridyl sulfone: a versatile carbonyl gem-difluoroolefination reagent
Gao B, et al.
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 2(2), 163-168 (2015)
Difluoromethyl 2?Pyridyl Sulfone
e-EROS Encyclopedia of Reagents for Organic Synthesis (2016)
Yanchuan Zhao et al.
Organic letters, 12(7), 1444-1447 (2010-03-10)
Difluoromethyl 2-pyridyl sulfone, a previously unknown compound, was found to act as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. It was found that the fluorinated sulfinate intermediate in the reaction is relatively stable, which can be
Difluoromethyl 2?Pyridyl Sulfone
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2016)
From difluoromethyl 2-pyridyl sulfone to difluorinated sulfonates: a protocol for nucleophilic difluoro(sulfonato)methylation.
G K Surya Prakash et al.
Angewandte Chemie (International ed. in English), 50(11), 2559-2563 (2011-03-04)
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