1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem SID
Reaxys RN
Togni Reagent II, Acid Togni CF3-Reagent
Trifluoromethylating Reagents
KUMI3F11
887144-94-7
MFCD18800706
253660048
11062788
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay(Analysis Method)
Appearance
Melting Point
Packaging
Storage
1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one
C8H4F3IO2
316.02
98%
White Solid
150-158°C
5g,10g,50g,100g,500g and 1kg
Store at room temperature (Diatomaceous earth included for reducing explosibility)
Togni reagent II is the second commerciallized and popularly-empolyed hypervalent  iodine CF3-reagent for electrophilic trifluoromethylation. This reagent can be applicable to vaious reaction substrates. e.g. the reaction of Togni Reagent II and olefins reportedly affords the corresponding allylic trifluoromethylated compounds. In particular, CF3-substituted vinylic cyclopropanes have been highly selectively formed by ustilizing Togni Reagent II. Such strained and unique cyclopropanes potentially bring the trifluoromethyl group to other useful organic skeletons by the selective cleavage of C–C bonds with an exclusive diastereoselectivity. Practically,Togni Reagent II contains diatomaceous earth due to reducing explosibility,by which it can be operationlly stored and shipped.
Its main difference from Alcohol CF3 reagent is higher crystallinity and lower solubility in organic solvents at comparable conditions. Polar solvents (typically THF, DCM, MeCN, alcohols, glymes) are preferrably utilized for reactions where Acid CF3-reagent is employed . When comparing the reactivity of the two Togni CF3-reagents, it is assumed that Alcohol CF3-reagent (Togni Reagent I) possesses less oxidative power than the related, more electron poor Acid CF3-reagent (Togni reagent II).
Novel 10-I-3 Hypervalent Iodine-Based Compounds for Electrophilic Trifluoromethylation. [1]
Copper-Catalyzed C(sp3)–C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation. [2]
Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents. [3]
Efficient trifluoromethylation via the cyclopropanation of allenes and subsequent C–C bond cleavage. [4]
Magnesium-Catalyzed Electrophilic Trifluoromethylation: Facile Access to All-Carbon Quaternary Centers in Oxindoles. [5]
References:
[1] P.Eisenberger, S.Gischig, A.Togni, Chem.Eur.J., 2006, 12, pp2579-2586.
[2] X.Wang, Y.Ye,S.Zhang, J.Feng, Y.Xu, Y.Zhang, J.Wang, J.Am.Chem.Soc., 2011, 133, pp16410-16413.
[3] J.Charpentier, N.Früh, A.Togni, Chem. Rev. ,2015, 115(2), pp 650-682.
[4] Y.Tang, Q.Yu, S.Ma, Org. Chem.Front., 2017, Advance Article.
[5] D.KatayevH.Kajita, A.Togni, Chem. Eur.J.2017, 23(35), pp 8353-8357.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
 Warning
H315,H319,H335,H373
P261,P305+P351+P338
2934.99.4400
NONH for all modes of transport

1. Product Specification
2. Safety Data Sheet

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