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Merck

746061

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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
329765740
MDL number:
MFCD17010193
Beilstein/REAXYS Number:
20317604

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Product Name

Difluoromethyl 2-pyridyl sulfone, 97% (HPLC)

InChI

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

SMILES string

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

InChI key

YRQNSTAWTLXCEZ-UHFFFAOYSA-N

assay

97% (HPLC)

form

solid

mp

44-49 °C

functional group

fluoro
sulfone

Quality Level

100

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This Item
403636442801392960
Difluoromethyl 2-pyridyl sulfone 97% (HPLC)

Sigma-Aldrich

746061

Difluoromethyl 2-pyridyl sulfone

N-(2-Pyridyl)bis(trifluoromethanesulfonimide) 96%

Sigma-Aldrich

403636

N-(2-Pyridyl)bis(trifluoromethanesulfonimide)

2-Hydroxy-5-(trifluoromethyl)pyridine 97%

Sigma-Aldrich

442801

2-Hydroxy-5-(trifluoromethyl)pyridine

Diphenyl-2-pyridylphosphine 97%

Sigma-Aldrich

392960

Diphenyl-2-pyridylphosphine

assay

97% (HPLC)

assay

96%

assay

97%

assay

97%

form

solid

form

solid

form

-

form

solid

mp

44-49 °C

mp

40-42 °C (lit.)

mp

145-149 °C (lit.)

mp

82-84 °C (dec.) (lit.)

functional group

fluoro

functional group

fluoro

functional group

fluoro

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

Reagent is used in the olefination of ketones and aldehydes to form gem-difluoro olefins under basic conditions.[1] Product is also used as a crucial intermediate toward making 1,1-difluorinated alkyl chains for the alkylation of heterocycles.[2]

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.[3][4]

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS3472
MKCK4291
MKCG2192
MKCG5596
MKBZ9524V

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Difluoromethyl 2?Pyridyl Sulfone
e-EROS Encyclopedia of Reagents for Organic Synthesis (2016)
Difluoromethyl 2?Pyridyl Sulfone
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2016)
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)
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)
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
View All Related Papers

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Hu Group – Prof. Product Portal

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

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