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Sigma-Aldrich

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

95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H10F3IO
CAS Number:
887144-97-0
Molecular Weight:
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

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H228,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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 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)
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
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)

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Related Content

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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