ChemicalBook--->CAS DataBase List--->1535-65-5

1535-65-5

1535-65-5 Structure

1535-65-5 Structure
IdentificationBack Directory
[Name]

[(Difluoromethyl)sulfonyl]benzene
[CAS]

1535-65-5
[Synonyms]

PhSO2CF2H
Phenyl difluoromethyl sulfone
Difluoromethyl phenyl sulfone
Difluoromethylphenylsulfone,95%
[(Difluoromethyl)sulfonyl]benzene
Difluoromethyl Phenyl Sulfone >
1-(difluoroMethylsulfonyl)benzene
Difluoromethyl phenyl sulfone >=97%
Benzene, [(difluoroMethyl)sulfonyl]-
[Molecular Formula]

C7H6F2O2S
[MDL Number]

MFCD01050170
[MOL File]

1535-65-5.mol
[Molecular Weight]

192.18
Chemical PropertiesBack Directory
[Melting point ]

24-25℃
[Boiling point ]

115-120 °C(Press: 7 Torr)
[density ]

1.348
[Fp ]

128℃
[refractive index ]

1.5000
[storage temp. ]

Keep in dark place,Inert atmosphere,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 DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/38
[Safety Statements ]

26-24/25
[WGK Germany ]

3
[TSCA ]

No
[HS Code ]

29309090
[Storage Class]

10 - Combustible liquids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
Hazard InformationBack Directory
[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.
[Reactions]

(1) Difluoromethylation of alkyl halides.
Difluoromethyl phenyl sulfone
(2) Difluoromethylation of aldehydes and ketones.
Difluoromethyl phenyl sulfone
(3) Difluoromethylenation of aldimines and ketimines.
Difluoromethyl phenyl sulfone
(4) Difluoromethylation of cyclic sulfates and sulfamidates.
Difluoromethyl phenyl sulfone
(5) (Phenylsulfonyl)difluoromethylation of carboxylic acid esters.
Difluoromethyl phenyl sulfone
(6) Difluoromethylenation of alkyl halides.
Difluoromethyl phenyl sulfone
(7) Difluoromethylenation of aromatic aldehydes.
Difluoromethyl phenyl sulfone
[Synthesis]

[(difluoromethyl)thio]benzene

1535-67-7

Difluoromethyl phenyl sulfone

1535-65-5

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.
Spectrum DetailBack Directory
[Spectrum Detail]

Difluoromethyl phenyl sulfone(1535-65-5)1HNMR
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