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Key Documents

119474

Sigma-Aldrich

N-Hydroxyurethane

Synonym(s):

N-Carbethoxyhydroxylamine, Ethyl N-hydroxycarbamate, Hydroxycarbamic acid ethyl ester, NSC 71045, NSC 83629

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About This Item

Linear Formula:
HONHCOOCH2CH3
CAS Number:
Molecular Weight:
105.09
Beilstein:
1747529
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

refractive index

n20/D 1.445 (lit.)

bp

113-116 °C/3 mmHg (lit.)

storage temp.

−20°C

SMILES string

CCOC(=O)NO

InChI

1S/C3H7NO3/c1-2-7-3(5)4-6/h6H,2H2,1H3,(H,4,5)

InChI key

VGEWEGHHYWGXGG-UHFFFAOYSA-N

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Application

N-Hydroxyurethane was used to synthesize N-methyl-O-benzylhydroxylamine and N-isopropyl-O-methylhydroxylamine.
Reactant involved in:
  • Synthesis of molecules used for intermolecular Sharpless aminohydroxylation reactions
  • Intermolecular ortho-C-H amidation of anilides
  • Cinchona alkaloid-catalyzed asymmetric cycloaddition
  • Allylic arylation

Biochem/physiol Actions

N-Hydroxyurethane causes the chromosomal fragmentation at millimolar concentrations and cell toxicity in cultured normal human leukocytes.

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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