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922722

Sigma-Aldrich

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:
1293990-73-4
Molecular Weight:
267.22
UNSPSC Code:
12352106
NACRES:
NA.22

form

solid

Quality Level

100

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.

Other Notes

Hydroxylamine-Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron Catalyzed Preparation of Unprotected Sulfinamides from Thiols

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C–H Amination

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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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