oxirane-2-carboxamide

• ChemBase ID: 157391
• Molecular Formular: C3H5NO2
• Molecular Mass: 87.0773
• Monoisotopic Mass: 87.03202841
• SMILES: C1C(O1)C(=O)N
• Canonical SMILES: NC(=O)C1CO1
• InChI: InChI=1S/C3H5NO2/c4-3(5)2-1-6-2/h2H,1H2,(H2,4,5)
• InChIKey: FMAZQSYXRGRESX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxirane-2-carboxamide
• IUPAC Traditional name: oxirane-2-carboxamide
• Synonyms: Oxiranecarboxamide; Glycidamide; Oxiranecarboxamide, Glycidic Acid Amide; Glycidamide; 环氧丙酰胺

Database IDs

• CAS Number: 5694-00-8
• EC Number: 227-163-2
• MDL Number: MFCD00468053
• Beilstein Number: 227 163 2
• PubChem SID: 162251528
• PubChem CID: 91550

CALCULATED PROPERTIES

• Acid pKa: 15.253758
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.1639786
• LogD (pH = 7.4): -1.1639786
• Log P: -1.1639786
• Molar Refractivity: 18.6956 cm^3
• Polarizability: 7.540291 Å^3
• Polar Surface Area: 55.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Water
• Apperance: White to pale Orange Solid
• Melting Point: 32-34°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: MB3200000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-46-22-36/37/38-43
• Safety Statements: 53-26-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H317-H319-H335-H350
• GHS Precautionary statements: P201-P261-P280-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (TLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C3H5NO2

DETAILS

Sigma Aldrich - 04704

Other Notes
In the summer of 2008 research scientists at the Technical University of Munich besides acrylamide detected glycidamide in potato crisps. Glycidamide is a metabolite of acrylamide.

Toronto Research Chemicals - G615250

An epoxide metabolite of acrylamide. It is neurotoxic and carcinogenic.

REFERENCES

• Costa, L.G., et al.: Toxicology, 98, 151 (1995)