All Photos(1)

119474

Sigma-Aldrich

N-Hydroxyurethane

Synonym(s):
Hydroxycarbamic acid ethyl ester, NSC 71045, N-Carbethoxyhydroxylamine, Ethyl N-hydroxycarbamate, NSC 83629
Linear Formula:
HONHCOOCH2CH3
CAS Number:
Molecular Weight:
105.09
Beilstein:
1747529
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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
N-Hydroxyurethane was used to synthesize N-methyl-O-benzylhydroxylamine and N-isopropyl-O-methylhydroxylamine.

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.

Storage Class Code

10 - Combustible liquids

WGK Germany

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

Certificate of Analysis

Certificate of Origin

Katsuhisa Sakano et al.
Free radical biology & medicine, 33(5), 703-714 (2002-09-05)
Carcinogenic urethane (ethyl carbamate) forms DNA adduct via epoxide, whereas carcinogenic methyl carbamate can not. To clarify a mechanism independent of DNA adduct formation, we examined DNA damage induced by N-hydroxyurethane, a urethane metabolite, using 32P-5'-end-labeled DNA fragments. N-hydroxyurethane induced...
Induction of chromosome breaks in cultured normal human leukocytes by potassium arsenite, hydroxyurea and related compounds.
J J Oppenheim et al.
Cancer research, 25(7), 980-985 (1965-08-01)
Timing of chemically induced neoplasia in mice revealed by the antineoplastic action of caffeine.
T Nomura
Cancer research, 40(4), 1332-1340 (1980-04-01)
K Tatsumi et al.
Journal of pharmacobio-dynamics, 5(11), 916-920 (1982-11-01)
The present study demonstrated the metabolism of N-hydroxyurethane by cell-free preparations, i.e., 9000 X g supernatant, cytosol and microsomes, from guinea pig livers. Under anaerobic conditions, the metabolizing activities of these preparations were enhanced markedly by addition of both an...
S Rossberger et al.
Mutation research, 145(3), 201-207 (1985-05-01)
N-Hydroxyurea and two structurally related compounds, acetohydroxamic acid and N-hydroxyurethane, were investigated for their potential to induce DNA repair synthesis in primary rat hepatocyte cultures. Repair was determined as repair replication by means of the bromodeoxyuridine density-shift method and, in...

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