Difluoromethyl 2-pyridyl sulfone Chemical Properties

Melting point:

47.0 to 51.0 °C

Boiling point:

324.4±42.0 °C(Predicted)

Density 

1.423±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-2.60±0.19(Predicted)

color 

Off-White

BRN 

20317604

Safety Information

Hazard Codes 

T

Risk Statements 

25-36

Safety Statements 

26-45-24/25

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HS Code 

29339900

Difluoromethyl 2-pyridyl sulfone Usage And Synthesis

Description

Difluoromethyl 2-pyridyl sulfone, also known as Hu reagent, is a novel and efficient gem-difluoroolefination reagent for preparing gem-difluoroalkenes from both aldehydes and ketones. The fluorinated sulfinate intermediates during the gem-difluoroolefination is relatively stable, and can be halogenated in situ to afford bromo- and iododifluoromethyl compounds. It can also act as nucleophilic difluoro(sulfonato)methylation reagent for the synthesis of α,α-difluorosulfonates from aldehydes, and alkyl halides and triflates.

Uses

2-[(Difluoromethyl)sulfonyl]pyridine is a new novel gem-difluoroolefination reagent for both aldehydes and ketones.

Uses

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.

Reactions

(1) gem-Difluoroolefination of aldehydes and ketones.

(2) Halodifluoromethylation of aldehydes and ketones.

(3) (Fluorosulfonyl)difluoromethylation of aldehydes and ketones.

(4) Difluoro(sulfonato)methylation of alkyl halides and triflates.

(5) Aromatic difluoromethylation

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.

References

[1] WENJUN MIAO. Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone[J]. Organic Letters, 2021, 23 3: 711-715. DOI:10.1021/acs.orglett.0c03939.
[2] WENJUN MIAO. Nucleophilic Iododifluoromethylation of Carbonyl Compounds Using Difluoromethyl 2-Pyridyl Sulfone[J]. Organic Letters, 2016, 18 11: 2766-2769. DOI:10.1021/acs.orglett.6b01258.
[3] YANCHUAN ZHAO. Difluoromethyl 2-Pyridyl Sulfone: A New gem-Difluoroolefination Reagent for Aldehydes and Ketones[J]. Organic Letters, 2010, 12 7: 1444-1447. DOI:10.1021/ol100090r.

Difluoromethyl 2-pyridyl sulfone(1219454-89-3)Related Product Information

• Difluoromethyl phenyl sulfone
• Fluoromethyl phenyl sulfone
• BroModifluoroMethyl phenyl sulfone
• FluoroMethyl 2-pyridyl sulfone