2-(2-methyl-5-nitro-1H-imidazol-1-yl)(2H4)ethan-1-ol

• ChemBase ID: 136330
• Molecular Formular: C6H9N3O3
• Molecular Mass: 171.15396
• Monoisotopic Mass: 171.06439116
• SMILES: C(CO)n1c(ncc1[N+](=O)[O-])C
• Canonical SMILES: OCCn1c(C)ncc1[N+](=O)[O-]
• InChI: InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
• InChIKey: VAOCPAMSLUNLGC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)(^2H₄)ethan-1-ol
• IUPAC Traditional name: 2-(2-methyl-5-nitroimidazol-1-yl)(^2H₄)ethanol
• Synonyms: 2-Methyl-5-nitroimidazole-1-ethanol-d4; Metronidazole-(ethylene-d4); 2-Methyl-5-nitro-1H-imidazole-1-(ethanol-d4); Anagiardil-d4; Arilin-d4; Bayer 5360-d4; Cimetrol 500LPCI-d4; Clont-d4; Deflamon-d4; Dentamet Gel-d4; Efloran-d4; Elyzol-d4; Entizol-d4; Flagesol-d4; Flagil-d4; 1-(2-Hydroxyethyl-d4)-2-methyl-5-nitroimidazole; NSC 50364-d4; NSC 69587-d4; Nidazole-d4; Metronidazole-d4

Database IDs

• CAS Number: 1261392-47-5
• MDL Number: MFCD08063466
• PubChem SID: 162230600
• PubChem CID: 49849778

CALCULATED PROPERTIES

• Acid pKa: 15.436296
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.46084404
• LogD (pH = 7.4): -0.45932958
• Log P: -0.45931023
• Molar Refractivity: 41.2205 cm^3
• Polarizability: 15.243772 Å^3
• Polar Surface Area: 83.87 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 151-153°C; 159-161 °C(lit.)
• Mass Shift: M+4

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281

Product Information

• Purity: 97% (CP)
• Isotopic Purity: 98 atom % D
• Mol. Weight: mol wt 175.10 by atom % calculation
• Empirical Formula (Hill Notation): C6D4H5N3O3

DETAILS

Sigma Aldrich - 696951

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - M338882

Labelled Metronidazole (M338880). Used as an antibacterial in the treatment of rosacea. Antiprotozoal (trichomonas). A potential human carcinogen.

REFERENCES

• Carballo, M., et al.: J. App. Toxicol., 29, 248 (2009)
• Leitsch, D., et al.: Mol. Microbiol., 72, 518 (2009)
• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2009)