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754218

Sigma-Aldrich

3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole

98%

Synonyme(s) :

1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Togni’s Reagent

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About This Item

Formule empirique (notation de Hill):
C10H10F3IO
Numéro CAS:
887144-97-0
Poids moléculaire :
330.09
Numéro MDL:
MFCD10567056
Code UNSPSC :
12352101
ID de substance PubChem :
329766407
Nomenclature NACRES :
NA.22

Pureté

98%

Forme

powder

Pf

75-79 °C

Température de stockage

2-8°C

Chaîne SMILES 

CC1(C)O[I](c2ccccc12)C(F)(F)F

InChI

1S/C10H10F3IO/c1-9(2)7-5-3-4-6-8(7)14(15-9)10(11,12)13/h3-6H,1-2H3

Clé InChI

HVAPLSNCVYXFDQ-UHFFFAOYSA-N

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Application

  • Selective trifluoromethylation of 1,3-disubstituted arenes through iridium-catalyzed arene borylation and copper-catalyzed trifluoromethylation
  • Copper-catalyzed trifluoromethylation of aryl- and alkenylboronic acids with electrophilic trifluoromethylating reagent
  • Pd-catalyzed electrophilic ortho-trifluoromethylation of arenes using trifluoroacetic acid as a promotor

Used in the Preparation of
  • Trifluoromethylimidoylethyl substituted heterocycles via bis(trifluoromethylsulfonyl)amine-catalyzed Rotter type reaction of heterocycles with nitriles in presence of trifluoromethylbenziodoxole
  • Stereoselective synthesis of α-trifluoromethyl aldehydes via trimethylbenzylimidazolidinone and copper-catalyzed enantioselective α-trifluoromethylation of aldehydes with iodonium salts

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Warning

Mentions de danger

H228,H315,H319,H335

Classification des risques

Eye Irrit. 2 - Flam. Sol. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

4.1B - Flammable solid hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

A Ritter-type reaction: direct electrophilic trifluoromethylation at nitrogen atoms using hypervalent iodine reagents.
Katrin Niedermann et al.
Angewandte Chemie (International ed. in English), 50(5), 1059-1063 (2011-01-27)
Tianfei Liu et al.
Angewandte Chemie (International ed. in English), 51(2), 540-543 (2011-12-01)
The old one two: A sequential iridium-catalyzed borylation and copper-catalyzed trifluoromethylation of arenes is described (see scheme; Pin = pinacol). The reaction is conducted under mild reaction conditions and tolerates a variety of functional groups. The advantages of this tandem
Tianfei Liu et al.
Organic letters, 13(9), 2342-2345 (2011-04-09)
A copper-catalyzed trifluoromethylation of aryl- and alkenylboronic acids with Togni's reagent was described. The reaction proceeded in good to excellent yields for a range of different substrates including heteroarylboronic acids and substrates with a variety of functional groups under mild
Xisheng Wang et al.
Journal of the American Chemical Society, 132(11), 3648-3649 (2010-02-27)
A Pd(II)-catalyzed C-H activation/trifluoromethylation of arenes with an electrophilic trifluoromethylation reagent using diverse heterocycle directing groups is reported. The presence of trifluoroacetic acid is crucial for this catalytic reaction.
Anna E Allen et al.
Journal of the American Chemical Society, 132(14), 4986-4987 (2010-03-20)
An enantioselective organocatalytic alpha-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical

Contenu apparenté

Togni Group – Professor Product Portal

Research in the Togni group focuses on the development of new ligands and reagents. These two general directions thus impact the ability to construct molecules in more efficient or unprecedented ways.

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