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Sigma-Aldrich

Difluoromethyl phenyl sulfone

≥97%

Synonyme(s) :

PhSO2CF2H, [(Difluoromethyl)sulfonyl]benzene

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About This Item

Formule empirique (notation de Hill):
C7H6F2O2S
Numéro CAS:
1535-65-5
Poids moléculaire :
192.18
Numéro Beilstein :
2259218
Numéro MDL:
MFCD01050170
Code UNSPSC :
12352101
ID de substance PubChem :
329765583
Nomenclature NACRES :
NA.22

Pureté

≥97%

Forme

solid

Chaîne SMILES 

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

Clé InChI

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

264.0 °F

Point d'éclair (°C)

128.9 °C

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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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Contenu apparenté

Hu Group – Professor Product Portal

The major research interests of Prof. Jinbo Hu's lab include the development of new fluorination reagents and reactions, especially the difluoromethylation, difluoromethylenation, and monofluoromethylation methods.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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