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696641

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

Name: 3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

329761847

UNSPSC Code:

12352101

MDL number:

MFCD10567056

Assay:

95%

Form:

powder

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Quality Level

100

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

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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Related Categories

C-C Bond Forming Reagents

Chemical Synthesis

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

pictograms

GHS02,GHS07

signalword

Warning

hcodes

H228,H315,H319,H335

pcodes

P210 - P302 + P352 - P305 + P351 + P338

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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Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(iii)-CF(3) reagents.

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)

Direct electrophilic N-trifluoromethylation of azoles by a hypervalent iodine reagent.

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)

Articles

Fluoroalkylation: Expansion of Togni Reagents

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

氟烷基化：Togni试剂的扩展

目前的氟烷基化工具包括Togni试剂、高价碘全氟烷基化试剂、氟烷基溴化物、硅烷类和羧酸盐类以及用于后期氟烷基化的磺酰氟类。

Global Trade Item Number

SKU	GTIN
696641-250MG	04061832785608
696641-5G	04061833338353
696641-1G	04061832785554

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