ethyl N-hydroxycarbamate

• ChemBase ID: 92468
• Molecular Formular: C3H7NO3
• Molecular Mass: 105.09258
• Monoisotopic Mass: 105.04259309
• SMILES: ONC(=O)OCC
• Canonical SMILES: CCOC(=O)NO
• InChI: InChI=1S/C3H7NO3/c1-2-7-3(5)4-6/h6H,2H2,1H3,(H,4,5)
• InChIKey: VGEWEGHHYWGXGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl N-hydroxycarbamate
• IUPAC Traditional name: N-hydroxyurethane
• Synonyms: N-Carbethoxyhydroxylamine; Hydroxycarbamic acid ethyl ester; NSC 71045; NSC 83629; Ethyl N-hydroxycarbamate; N-Hydroxyurethane; N-Hydroxyurethane; Ethyl hydroxycarbamate 97%; Hydroxyurethane; NSC-71045; NSC-83629; SQ 16819; N-Hydroxy-carbamic Acid Ethyl Ester; Hydroxyurethane; N-羟基氨基甲酸乙酯; N-羟基尿烷

Database IDs

• CAS Number: 589-41-3
• EC Number: 209-648-0
• MDL Number: MFCD00002108
• Beilstein Number: 1747529
• PubChem SID: 24847397; 24880282; 162079166
• PubChem CID: 11510

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 8.474469
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.05782742
• LogD (pH = 7.4): -0.09218932
• Log P: -0.057370964
• Molar Refractivity: 22.6027 cm^3
• Polarizability: 8.944007 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 2

PROPERTIES

Physical Property

• Solubility: Diethyl Ether; Dimethyl Sulfoxide; Water
• Apperance: Yellow Oil
• Boiling Point: 113-116 °C/3 mmHg(lit.); 113-116°C/3mm
• Flash Point: >110°C; 113 °C; 235.4 °F
• Refractive Index: 1.445; n20/D 1.445(lit.)

Safety Information

• Storage Warning: Toxic/Carcinogenic/Store at -20°C
• RTECS: FB1750000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (CHN)
• Grade: technical
• Shipped in: wet ice
• Linear Formula: HONHCOOCH2CH3

DETAILS

Sigma Aldrich - 119474

Packaging
5, 25 g in glass bottle
Application
Reactant involved in:
• Synthesis of molecules used for intermolecular Sharpless aminohydroxylation reactions1
• Intermolecular ortho-C-H amidation of anilides2
• Cinchona alkaloid-catalyzed asymmetric cycloaddition3
• Allylic arylation4

Sigma Aldrich - 56620

Application
Reactant involved in:
• Synthesis of molecules used for intermolecular Sharpless aminohydroxylation reactions1
• Intermolecular ortho-C-H amidation of anilides2
• Cinchona alkaloid-catalyzed asymmetric cycloaddition3
• Allylic arylation4

Toronto Research Chemicals - H991050

Metabolite of carcinogenic Urethane (U825300).

REFERENCES

• Sakano, K. et al.: Free Radical Bio. Med. 33, 703 (2002).