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MilliporeSigma

696641

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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$131.00

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$486.00

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$938.00

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About This Item

Empirical Formula (Hill Notation):
C10H10F3IO
CAS Number:
887144-97-0
Molecular Weight:
330.09
NACRES:
NA.22
PubChem Substance ID:
329761847
UNSPSC Code:
12352101
MDL number:
MFCD10567056
Assay:
95%
Form:
powder

Key Documents

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InChI key

HVAPLSNCVYXFDQ-UHFFFAOYSA-N

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

assay

95%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

75-79 °C

functional group

fluoro, iodo

storage temp.

2-8°C

Quality Level

100

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1 of 4

This Item
488712559873284548
3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole 95%

Sigma-Aldrich

696641

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

Trimethyl(trifluoromethyl)silane 99%

Sigma-Aldrich

488712

Trimethyl(trifluoromethyl)silane

Dess-Martin periodinane solution 0.3 M in methylene chloride

Sigma-Aldrich

559873

Dess-Martin periodinane solution

3,4-(Methylenedioxy)toluene 97%

Sigma-Aldrich

284548

3,4-(Methylenedioxy)toluene

assay

95%

assay

99%

assay

-

assay

97%

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

-

reaction suitability

-

form

powder

form

-

form

-

form

liquid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

mp

75-79 °C

mp

-

mp

-

mp

-

Application

Easily accessible hypervalent iodine compound acting as an electrophilic CF3-transfer reagent for direct, mild, and efficient trifluoromethylation.[1]

Trifluoromethylation of a variety of compounds including:
  • Secondary and primary aryl- and alkylphospines[1]
  • Phenols[2]
  • Peptides containing cysteine residudes by SPPS and electrophilic S-trifluoromethylation[3]
  • Arenes and N-heterocycles[4]
  • Electrophilic N-trifluoromethylation of Arozoles[5]

related product

Product No.
Description
Pricing

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS2079
MKCR5189
MKCJ4362
MKCJ0020
MKCJ1881

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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)
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)
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)

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