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Sigma-Aldrich

Difluoromethyl phenyl sulfone

≥97%

Synonym(s):

PhSO2CF2H, [(Difluoromethyl)sulfonyl]benzene

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About This Item

Empirical Formula (Hill Notation):
C7H6F2O2S
CAS Number:
1535-65-5
Molecular Weight:
192.18
Beilstein:
2259218
MDL number:
MFCD01050170
UNSPSC Code:
12352101
PubChem Substance ID:
329765583
NACRES:
NA.22

Assay

≥97%

form

solid

SMILES string

FC(F)S(=O)(=O)c1ccccc1

InChI

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

InChI key

LRHDNAVPELLXDL-UHFFFAOYSA-N

Application

Reagent Used for
  • Reductive silylation and the preparation of trifluoro- and difluoromethylsilanes by reductive coupling of fluoromethyl sulfones, sulfoxides and sulfides with chlorosilanes
  • Fluoroalkylation/chloroalkylation of α,β-enones, arynes, acetylenic ketones and other Michael acceptors
  • Difluoromethylation of primary alkyl halides via nucleophilic substitution-reductive desulfonylation

Reagent used in Preparation of
  • α-difluoromethyl amines via stereoselective (phenylsulfonyl)difluoromethylation of chiral sulfinyl aldimines
  • Anti-difluoropropanediols via potassium tert-butoxide-catalyzed difluoromethylenation of aldehydes
  • β-difluoromethylated and β-difluoromethylenated alcohols and amines by regioselective nucleophilic difluoromethylation of 1,2-cyclic sulfates and sulfamidates
  • Difluoroalkenes from alkyl halides via nucleophilic substitution-elimination
  • Difluoromethyl alcohol derivatives from enolizable and non-enolizable carbonyl compounds using nucleophilic phenylsulfonyldifluoromethylation-reductive desulfonylation strategy
  • Fluoromethylated vicinal ethylenediamines via fluoromethylation of chiral α-aminobutanesulfinimines with (phenylsulfonyl)fluoromethanes followed by reductive desulfonylation and alcoholysis

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

264.0 °F

Flash Point(C)

128.9 °C

Certificates of Analysis (COA)

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Difluoromethyl phenyl sulfone as a selective difluoromethylene dianion equivalent: one-pot stereoselective synthesis of anti-2,2-difluoropropane-1,3-diols.
G K Surya Prakash et al.
Angewandte Chemie (International ed. in English), 42(42), 5216-5219 (2003-11-06)
Jun Liu et al.
The Journal of organic chemistry, 72(8), 3119-3121 (2007-03-28)
The diastereoselective nucleophilic (phenylsulfonyl)difluoromethylation and (phenylsulfonyl)monofluoromethylation of alpha-amino N-tert-butanesulfinimines (3) by using PhSO2CF2H and PhSO2CH2F reagents gave products 4 or 5 in high yields (73-99%) and with excellent diastereoselectivity (dr up to >99:1). After subsequent reductive desulfonylation and acid-catalyzed alcoholysis
A remarkably efficient fluoroalkylation of cyclic sulfates and sulfamidates with PhSO2CF2H: facile entry into beta-difluoromethylated or beta-difluoromethylenated alcohols and amines.
Chuanfa Ni et al.
Angewandte Chemie (International ed. in English), 46(5), 786-789 (2006-12-14)
Facile synthesis of chiral alpha-difluoromethyl amines from N-(tert-butylsulfinyl)aldimines.
Ya Li et al.
Angewandte Chemie (International ed. in English), 44(36), 5882-5886 (2005-09-09)
G K Surya Prakash et al.
Organic letters, 6(23), 4315-4317 (2004-11-05)
A facile and efficient nucleophilic difluoromethylation of primary alkyl halides has been disclosed through a novel nucleophilic substitution-reductive desulfonylation strategy, using difluoromethyl phenyl sulfone as a difluoromethyl anion ("CF(2)H(-)") equivalent.
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