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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:
589-41-3
Molecular Weight:
105.09
Beilstein:
1747529
EC Number:
209-648-0
MDL number:
MFCD00002108
UNSPSC Code:
12352100
PubChem Substance ID:
24847397
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals.
Kaba RA and Ingold KU
Journal of the American Chemical Society, 98(23), 7375-7380 (1976)
P M Weiss et al.
Biochemistry, 23(19), 4346-4350 (1984-09-11)
The true substrate for the pyruvate kinase catalyzed phosphorylation of hydroxylamine at high pH which is activated by bicarbonate is shown to be N-hydroxycarbamate, since a lag is seen when the reaction is started by the addition of bicarbonate or
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
T Nomura et al.
Cancer research, 43(11), 5156-5162 (1983-11-01)
To learn the effects of tumor inhibitors on chemically induced malformations, caffeine, antipain, and 13-trans-retinoic acid were given to pregnant ICR/Jcl mice after a single dose of urethan, N-hydroxyurethan, N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea, or 4-nitroquinoline 1-oxide, which induces about 50% of the
K Sugihara et al.
Journal of pharmacobio-dynamics, 6(9), 677-683 (1983-09-01)
The present study provides the evidence that liver aldehyde oxidase in the presence of its electron donors can catalyze the reduction of N-hydroxyurethane to urethane under anaerobic conditions. Guinea pig liver 9000 X g supernatant and cytosol, but not liver
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