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Fluoromethyl phenyl sulfone

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Fluoromethyl phenyl sulfone Basic information

Product Name:
Fluoromethyl phenyl sulfone
Synonyms:
  • Fluoromethanesulfonyl-benzene
  • FLUOROMETHYL PHENYL SULFONE
  • FLUOROMETHYLSULFONYLBENZENE
  • Phenyl Fluoromethyl Sulfone
  • FluoromethylPhenylSulfone>
  • Benzene, [(fluoromethyl)sulfonyl]-
CAS:
20808-12-2
MF:
C7H7FO2S
MW:
174.19
Product Categories:
  • Biochemistry
  • Fluorinated Building Blocks
  • Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds
  • Reagents for Oligosaccharide Synthesis
  • Sulfur Compounds (for Synthesis)
  • Synthetic Organic Chemistry
Mol File:
20808-12-2.mol
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Fluoromethyl phenyl sulfone Chemical Properties

Melting point:
53 °C
Boiling point:
151 °C(Press: 0.3 Torr)
Density 
1.274±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
soluble in Methanol
form 
powder to crystal
color 
White to Almost white
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Safety Information

Safety Statements 
24/25
HS Code 
29309090
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Fluoromethyl phenyl sulfone Usage And Synthesis

Description

Fluoromethyl phenyl sulfone is a useful nucleophilic monofluoromethylation reagent for the synthesis of fluoromethyl alcohols and amines. In the nucleophilic reaction step, strong bases such as LiHMDS and n-BuLi are used to generate the nucleophilic (phenylsulfonyl)fluoromethyl anion. In the desulfonylation step, sodium/mercury amalgam and magnesium are the commonly used reductive reagents. Besides, the addition reaction between fluoromethyl phenyl sulfone and carbonyls can be used to prepare monofluoroaklenes via acylation–elimination.

Uses

Fluoromethyl phenyl sulfone can be used to prepare monofluoroaklenes and chiral α-Monofluoromethyl Amines. Highly stereoselective nucleophilic monofluoromethylation of (R)-(tert-butanesulfinyl)imines with fluoromethyl phenyl sulfone was achieved to afford α-monofluoromethylamines with a nonchelation-controlled stereoselectivity mode. By using the same chemistry, (R)-(tert-butanesulfinyl)imines bearing a terminal tosylate (OTs) group can be converted to α-monofluoromethylated cyclic secondary amines with high stereoselectivity.

Reactions

(1) Monofluoromethylation of aldehydes and ketones.

(2) Monofluoromethylation of aldimines and ketimines.

(3) Monofluoromethylenation of aldehydes and ketones.

(4) (Phenylsulfonyl)fluoromethylation of esters.

References

[1] YA LI. Stereoselective Nucleophilic Monofluoromethylation of N-(tert-Butanesulfinyl)imines with Fluoromethyl Phenyl Sulfone[J]. Organic Letters, 2006. DOI:10.1021/ol060322t.
[2] M. INBASEKARAN. ChemInform Abstract: A NOVEL AND EFFICIENT SYNTHESIS OF FLUOROMETHYL PHENYL SULFONE AND ITS USE AS A FLUOROMETHYL WITTIG EQUIVALENT[J]. ChemInform, 1985. DOI:10.1002/chin.198536160.
[3] GOUVERNEUR V, LOZANO ó. Preparation of Chiral α-Monofluoromethyl Amines Using Fluoromethyl Phenyl Sulfone[C]. 1900. DOI:10.1055/sos-SD-203-00578.

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