Fluoromethyl phenyl sulfone

Bezeichnung:Fluoromethyl phenyl sulfone

CAS-Nr20808-12-2

Englisch Name:Fluoromethyl phenyl sulfone

CBNumberCB7230066

SummenformelC7H7FO2S

Molgewicht174.19

MOL-Datei20808-12-2.mol

Fluoromethyl phenyl sulfone physikalisch-chemischer Eigenschaften

Schmelzpunkt	53 °C
Siedepunkt	151 °C(Press: 0.3 Torr)
Dichte	1.274±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	soluble in Methanol
Aggregatzustand	powder to crystal
Farbe	White to Almost white

Sicherheit

S-Sätze:	24/25
HS Code	29309090

Gefahreninformationscode (GHS)

Fluoromethyl phenyl sulfone Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Verwenden
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.
Reaktionen
(1) Monofluoromethylation of aldehydes and ketones.

(2) Monofluoromethylation of aldimines and ketimines.

(3) Monofluoromethylenation of aldehydes and ketones.

(4) (Phenylsulfonyl)fluoromethylation of esters.
Einzelnachweise
[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.

Fluoromethyl phenyl sulfone Upstream-Materialien And Downstream Produkte

Fluoromethyl phenyl sulfone Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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