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696641

Sigma-Aldrich

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

95%

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:
887144-97-0
Peso molecular:
330.09
MDL number:
MFCD10567056
UNSPSC Code:
12352101
PubChem Substance ID:
329761847
NACRES:
NA.22

assay

95%

form

powder

reaction suitability

reaction type: C-C Bond Formation

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

Easily accessible hypervalent iodine compound acting as an electrophilic CF3-transfer reagent for direct, mild, and efficient trifluoromethylation.

Trifluoromethylation of a variety of compounds including:
  • Secondary and primary aryl- and alkylphospines
  • Phenols
  • Peptides containing cysteine residudes by SPPS and electrophilic S-trifluoromethylation
  • Arenes and N-heterocycles
  • Electrophilic N-trifluoromethylation of Arozoles

Related product

Referencia del producto
Descripción
Precios

pictograms

FlameExclamation mark
GHS02,GHS07

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Patrick Eisenberger et al.
Chemical communications (Cambridge, England), 13(13), 1575-1577 (2008-03-21)
A direct, mild and efficient trifluoromethylation of primary and secondary phosphines is achieved with easily accessible, cheap hypervalent iodine compounds acting as electrophilic CF(3)-transfer reagents.
Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents
Wiehn, M. S.; Vinogradova, E. V.; Togni, A.
Journal of Fluorine Chemistry, 131, 951-957 (2010)
Electrophilic S-trifluoromethylation of cysteine side chains in a- and ?-peptides: isolation of trifluoromethylated Sandostatin (octreotide) derivatives
Capone, S.; et al.
Helvetica Chimica Acta, 91, 2035-2056 (2008)
Reactivity of a 10-I-3 Hypervalent Iodine Trifluoromethylation Reagent With Phenols
Stanek, K.; Koller, R.; Togni, A.
The Journal of Organic Chemistry, 19, 7678-7685 (2008)
Katrin Niedermann et al.
Angewandte Chemie (International ed. in English), 51(26), 6511-6515 (2012-05-23)
Effective CF(3) transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed

Artículos

Fluoroalkylation: Expansion of Togni Reagents

Fluoroalkylation toolbox expands with various reagents for late-stage fluoroalkylation in organic synthesis and medicinal chemistry.

Fluoroalkylation: Expansion of Togni Reagents

Fluoroalkylation toolbox expands with various reagents for late-stage fluoroalkylation in organic synthesis and medicinal chemistry.

Fluoroalkylation: Expansion of Togni Reagents

Fluoroalkylation toolbox expands with various reagents for late-stage fluoroalkylation in organic synthesis and medicinal chemistry.

Fluoroalkylation: Expansion of Togni Reagents

Fluoroalkylation toolbox expands with various reagents for late-stage fluoroalkylation in organic synthesis and medicinal chemistry.

Contenido relacionado

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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