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900624

Sigma-Aldrich

Di-t-butyl oxaziridine

≥95%

Synonym(s):

Kurti oxaziridine

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About This Item

Empirical Formula (Hill Notation):
C9H19NO
CAS Number:
56741-77-6
Molecular Weight:
157.25
UNSPSC Code:
12352000
NACRES:
NA.22

Quality Level

100

assay

≥95%

form

liquid

availability

available only in USA

refractive index

n/D 1.4453

density

0.90 g/mL

storage temp.

2-8°C

SMILES string

CC(C)(C)C1(NO1)C(C)(C)C

InChI

1S/C9H19NO/c1-7(2,3)9(10-11-9)8(4,5)6/h10H,1-6H3

Application

This oxaziridine has been used in synthetic methods for amination, heteroatom transfer, and C-H functionalization. Recently, the lab of Laszlo Kurti demonstrated its application for direct electrophilic primary and secondary amination of arylmetals in the presence of Cu(I) salts -- void of precious metal catalysts, ligands, protecting groups, or directing groups.

Other Notes

Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Diverse sp3 C-H functionalization through alcohol β-sulfonyloxylation

pictograms

Flame
GHS02

signalword

Danger

hcodes

H242

Hazard Classifications

Self-react. C

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

143.6 °F

flash_point_c

62 °C

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Synthesis of Alkoxylamines by Alkoxide Amination with 3,3'-Di-tert-butyloxaziridine.
Ingrid C. Choong et al.
The Journal of organic chemistry, 64(18), 6528-6529 (2001-10-25)
Zhe Zhou et al.
Journal of the American Chemical Society, 139(1), 115-118 (2016-12-23)
Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl- as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or directing
Yan Xu et al.
Nature chemistry, 7(10), 829-834 (2015-09-24)
Site-selective C-H functionalization has emerged as an attractive tool for derivatizing complex synthetic intermediates, but its use for late-stage diversification is limited by the functional groups that can be introduced, especially at unactivated sp(3)-hybridized positions. To overcome this, we introduce
Hongyin Gao et al.
Nature chemistry, 9(7), 681-688 (2017-06-24)
Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has

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