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119474 Sigma-Aldrich

N-Hydroxyurethane

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

  • CAS Number 589-41-3

  • Linear Formula HONHCOOCH2CH3

  • Molecular Weight 105.09

  •  Beilstein/REAXYS Number 1747529

  •  EC Number 209-648-0

  •  MDL number MFCD00002108

  •  PubChem Substance ID 24847397

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Nitrogen Compounds - Organic Building Blocks, Organic Building Blocks, Protected Amines More...
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

Description

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

Packaging

5, 25 g in glass bottle

Biochem/physiol Actions

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

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
FB1750000
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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