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Merck

754218

Sigma-Aldrich

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

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H10F3IO
Número de CAS:
Peso molecular:
330.09
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

assay

98%

form

powder

mp

75-79 °C

storage temp.

2-8°C

SMILES string

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

InChI key

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

related product

Referencia del producto
Descripción
Precios

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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.
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
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
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
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.

Contenido relacionado

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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