742600
Difluoromethyl phenyl sulfone
≥97%
Synonym(s):
PhSO2CF2H, [(Difluoromethyl)sulfonyl]benzene
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About This Item
Empirical Formula (Hill Notation):
C7H6F2O2S
CAS Number:
Molecular Weight:
192.18
Beilstein/REAXYS Number:
2259218
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
≥97%
form
solid
functional group
fluoro
sulfone
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
Reagent used in Preparation of
- 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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
264.0 °F
flash_point_c
128.9 °C
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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)
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)
Convenient synthesis of difluoromethyl alcohols from both enolizable and non-enolizable carbonyl compounds with difluoromethyl phenyl sulfone
Prakash, G. K. S.; et al.
European Journal of Organic Chemistry, 11, 2218-2223 (2005)
Difluoromethyl phenyl sulfone, a difluoromethylidene equivalent: use in the synthesis of 1,1-difluoro-1-alkenes.
G K Surya Prakash et al.
Angewandte Chemie (International ed. in English), 43(39), 5203-5206 (2004-09-30)
Related Content
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.
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
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