119474
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
209-648-0
Beilstein/REAXYS Number:
1747529
MDL number:
InChI key
VGEWEGHHYWGXGG-UHFFFAOYSA-N
InChI
1S/C3H7NO3/c1-2-7-3(5)4-6/h6H,2H2,1H3,(H,4,5)
SMILES string
CCOC(=O)NO
refractive index
n20/D 1.445 (lit.)
bp
113-116 °C/3 mmHg (lit.)
storage temp.
−20°C
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
10 - Combustible liquids
wgk
WGK 2
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves
Regulatory Information
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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
Comparative carcinogenicities and mutagenicities of vinyl carbamate, ethyl carbamate, and ethyl N-hydroxycarbamate.
G A Dahl et al.
Cancer research, 40(4), 1194-1203 (1980-04-01)
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
Y Sharief et al.
Mutation research, 126(2), 159-167 (1984-04-01)
Ethyl carbamate (EC) and two related carcinogens, ethyl N-hydroxycarbamate (ENHC) and vinyl carbamate (VC), caused species-specific increases in sister-chromatid exchange (SCE) formation in the bone marrow cells of rodents. Mice exposed to 400 mg/kg of EC had SCE increases of
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)
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