Difluoromethyl phenyl sulfone Chemical Properties

Melting point:

24-25℃

Boiling point:

115-120 °C(Press: 7 Torr)

Density 

1.348

refractive index 

1.5000

Flash point:

128℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

liquid

color 

colorless

Water Solubility 

Soluble in chloroform and water.

BRN 

2259218

InChI

InChI=1S/C7H6F2O2S/c8-7(9)12(10,11)6-4-2-1-3-5-6/h1-5,7H

InChIKey

LRHDNAVPELLXDL-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-24/25

WGK Germany 

3

TSCA 

No

HS Code 

29309090

Difluoromethyl phenyl sulfone Usage And Synthesis

Description

Difluoromethyl phenyl sulfone is a powerful nucleophilic difluoromethylation reagent due to the high reactivity of the sulfonyl-stabilized difluoromethyl anion towards many electrophiles including carbonyls, imines, alkyl halides, and cyclic sulfates and sulfamidates. In the nucleophilic reaction step, depending on the substrate structure, strong bases are used to generate the nucleophilic (phenylsulfonyl)difluoromethyl anion in situ. In the desulfonylation step, sodium/mercury amalgam and magnesium are the commonly used reductive reagents. Besides, the (phenylsulfonyl)difluoromethylated compounds can undergo β-elimination to afford gem-difluoroalkenes.

Chemical Properties

light yellow liquid

Uses

Efficient reagent for difluoromethylation of carbonyls and aldehydes.

Uses

Difluoromethyl Phenyl Sulfone has been used as a reagent for the nucleophilic difluoro(phenylsulfonyl)methylation of carbonyls

Reactions

(1) Difluoromethylation of alkyl halides.

(2) Difluoromethylation of aldehydes and ketones.

(3) Difluoromethylenation of aldimines and ketimines.

(4) Difluoromethylation of cyclic sulfates and sulfamidates.

(5) (Phenylsulfonyl)difluoromethylation of carboxylic acid esters.

(6) Difluoromethylenation of alkyl halides.

(7) Difluoromethylenation of aromatic aldehydes.

Synthesis

To an anhydrous dichloromethane (69 mL) solution of difluoromethyl phenyl sulfide (3.98 g, 25 mmol) was added solid m-chloroperoxybenzoic acid (m-CPBA, 15.9 g, 92.0 mmol) in batches at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, dichloromethane (50 mL) was added to dilute the mixture, and the mixture was washed sequentially with 10% aqueous sodium sulfite (2 × 100 mL), 5% aqueous sodium bicarbonate (4 × 50 mL) and saturated saline (2 × 100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane and hexane (3:1, v/v) as eluents. Thin layer chromatography (TLC) showed an Rf value of 0.40 (dichloromethane/hexane, 3:1). 4.24 g of difluoromethyl phenyl sulfone was finally obtained in 88% (22.1 mmol) yield. The structure of the product was confirmed by nuclear magnetic resonance hydrogen (1H NMR, 300 MHz, CDCl3), carbon (13C NMR, 101 MHz, CDCl3) and fluorine (19F NMR, 282 MHz, CDCl3) spectra, and the data were in agreement with the literature reports.

References

[1] G. PRAKASH. Nucleophilic difluoromethylation of primary alkyl halides using difluoromethyl phenyl sulfone as a difluoromethyl anion equivalent.[J]. Organic Letters, 2004. DOI:10.1002/CHIN.200509059.
[2] G. K. SURYA PRAKASH. Difluoromethyl Phenyl Sulfone, a Difluoromethylidene Equivalent: Use in the Synthesis of 1,1-Difluoro-1-alkenes.[J]. ChemInform, 2005. DOI:10.1002/chin.200504098.
[3] G. K. SURYA PRAKASH. Nucleophilic Difluoromethylation of Primary Alkyl Halides Using Difluoromethyl Phenyl Sulfone as a Difluoromethyl Anion Equivalent[J]. Organic Letters, 2004, 6 23: 4315-4317. DOI:10.1021/ol048166i.

Difluoromethyl phenyl sulfone(1535-65-5)Related Product Information

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