922722
O-Pivaloylhydroxyamine triflic acid
Synonym(s):
2,2-dimethyl-, azanyl ester, 1,1,1-trifluoromethanesulfonate, PivONH3OTF, Propanoic acid
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About This Item
Empirical Formula (Hill Notation):
C5H11NO2 · CHF3O3S
CAS Number:
Molecular Weight:
267.22
MDL number:
UNSPSC Code:
12352106
NACRES:
NA.22
InChI key
AJUKGKFBUGZGSW-UHFFFAOYSA-M
SMILES string
FC(F)(F)[S](=O)(=O)[O-].[N+H3]OC(=O)C(C)(C)C
form
solid
functional group
fluoro, triflate
Quality Level
Application
This hydroxylamine-based reagent enables the iron-catalyzed selective transformation of thiols to sulfinamides under mild conditions without the use of precious metal catalysts or additional oxidants. This reagent is shelf stable and facilitates the reaction in a single step and under mild conditions.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3
target_organs
Respiratory system
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Sayanti Chatterjee et al.
Angewandte Chemie (International ed. in English), 60(2), 758-765 (2020-09-22)
An iron catalyzed reaction for the selective transformation of thiols (-SH) to sulfinamides (-SONH2 ) by a direct transfer of -O and free -NH2 groups has been developed. The reaction operates under mild conditions using a bench stable hydroxylamine derived
Eric Falk et al.
Organic letters, 23(4), 1422-1426 (2021-02-06)
We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes.
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