N-Boc-hydroxylamine, 98+%

Name: N-Boc-hydroxylamine, 98+%
SKU: A10349.14
Price: 332.00 EUR

CAS: 36016-38-3 | C5H11NO3 | 133.15 g/mol

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Catalog number A10349.14

also known as A10349-14

Price (EUR)

332,00

Each

Quantity:

25 g

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Price (EUR)

332,00

Each

Chemical Identifiers

CAS36016-38-3

IUPAC Nametert-butyl N-hydroxycarbamate

Molecular FormulaC5H11NO3

InChI KeyDRDVJQOGFWAVLH-UHFFFAOYSA-N

SMILESCC(C)(C)OC(=O)NO

Specifications

Specification Sheet

Assay (GC)≥98.0%

Appearance (Color)White

FormCrystals or powder or crystalline powder

Identification (FTIR)Conforms

Melting Point (clear melt)52.0-58.0?C

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Slightly soluble in water.

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

RUO – Research Use Only

General 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.