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921947

Sigma-Aldrich

N-Sulfinyl-O-(tert-butyl)hydroxylamine

≥95%

Synonym(s):

t-BuONSO

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About This Item

Empirical Formula (Hill Notation):
C4H9NO2S
CAS Number:
2567792-04-3
Molecular Weight:
135.18
MDL number:
MFCD33021394
UNSPSC Code:
12352116

Quality Level

100

Assay

≥95%

form

liquid

refractive index

n/D 1.454

density

1.062 g/mL

storage temp.

−20°C

SMILES string

[S](=NOC(C)(C)C)=O

InChI

1S/C4H9NO2S/c1-4(2,3)7-5-8-6/h1-3H3

InChI key

QNDHWAYLAJVRCB-UHFFFAOYSA-N

Application

t-BuONSO is a stable reagent active for the synthesis of primary sulfonamides when used in conjunction with organolithium or Grignard reagents. t-BuONSO is tolerant of a variety of alkyl and aryl substrates and can be used in the synthesis of many medicinally relevant compounds.

Other Notes

Modular Sulfondiimine Synthesis Using a Stable Sulfinylamine Reagent


Harnessing Sulfinyl Nitrenes: A Unified One-Pot Synthesis of Sulfoximines and Sulfonimidamides


Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H242,H317,H334

Hazard Classifications

Resp. Sens. 1 - Self-react. C - Skin Sens. 1

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Thomas Q Davies et al.
Journal of the American Chemical Society, 142(36), 15445-15453 (2020-08-26)
Sulfoximines and sulfonimidamides are promising compounds for medicinal and agrochemistry. As monoaza analogues of sulfones and sulfonamides, respectively, they combine good physicochemical properties, high stability, and the ability to build complexity from a three-dimensional core. However, a lack of quick
Thomas Q Davies et al.
Organic letters, 22(24), 9495-9499 (2020-11-26)
Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents
Ze-Xin Zhang et al.
Journal of the American Chemical Society, 141(33), 13022-13027 (2019-08-10)
Sulfondiimines-the double aza-analogues of sulfones-hold significant potential as leads in discovery chemistry, yet their application in this arena has been held back by the scarcity of appropriate synthetic routes. Existing methods employ sulfides as substrates, and rely on consecutive imination

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