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36016-38-3 - N-Boc-hydroxylamine, 98+% - N-(tert-Butoxycarbonyl)hydroxylamine - tert-Butyl N-hydroxycarbamate - A10349 - Alfa Aesar

A10349 N-Boc-hydroxylamine, 98+%

CAS Number
36016-38-3
Synonyms
N-(tert-Butoxycarbonyl)hydroxylamine
tert-Butyl N-hydroxycarbamate

Size Price ($) Quantity Availability
1g 23.59
5g 81.58
25g 294.62
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N-Boc-hydroxylamine, 98+%

MDL
MFCD00002107
EINECS
252-836-2

Chemical Properties

Formula
(CH3)3COCONHOH
Formula Weight
133.15
Melting point
55-58°
Sensitivity
Moisture Sensitive
Solubility
Slightly soluble in water.

Applications

N-Boc-hydroxylamine is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts. It acts as a reagent for the synthesis of hydroxylamine derivatives t-butyl-N-(acyloxy)carbamates and N,O-diacylated N-hydroxyarylsulfonamides.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents, strong bases, reducing agents and alkali metals. Store in a cool place.

Literature References

Precursor of O-substituted hydroxylamines, including the unstable O-acyl and O-sulfonylhydroxylamines which, having a good leaving group on nitrogen, are powerful aminating agents: J. Am. Chem. Soc., 82, 3133 (1960); Tetrahedron, 29, 1063 (1973); Synthesis, 140 (1972). For a review of O-mesitylenesulfonylhydroxylamine and related compounds, see: Synthesis, 1 (1977).

Pariente-Cohen, N.; Weitman, M.; Tania, N.; Major, D. T.; Gottlieb, H. E.; Hoz, S.; Nudelman, A. Acylation or phosphorylation of hydroxyurea unexpectedly takes place on N rather than on O, leading to the formation of amides instead of the expected esters. RSC Adv. 2015, 5 (31), 24038-24043.

Gini, A.; Segler, M.; Kellner, D.; Mancheño, O. G. Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines. Chem. Eur. J. 2015, 21 (34), 12053-12060.

Other References

Beilstein
1756546
Harmonized Tariff Code
2922.19
TSCA
No

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