3-amino-1,2,4-benzotriazin-1-ium-1-olate

• ChemBase ID: 83226
• Molecular Formular: C7H6N4O
• Molecular Mass: 162.14874
• Monoisotopic Mass: 162.05416083
• SMILES: [n+]1(c2c(nc(n1)N)cccc2)[O-]
• Canonical SMILES: Nc1nc2ccccc2[n+](n1)[O-]
• InChI: InChI=1S/C7H6N4O/c8-7-9-5-3-1-2-4-6(5)11(12)10-7/h1-4H,(H2,8,9,10)
• InChIKey: BBRWGJRKAHEZBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-1,2,4-benzotriazin-1-ium-1-olate
• IUPAC Traditional name: 3-amino-1,2,4-benzotriazin-1-ium-1-olate
• Synonyms: 3-AMINO-1,2,4-BENZOTRIAZINE-1-OXIDE; 4-Desoxytirapazamine; 1,2,4-Benzotriazin-3-amine 1-Oxide; 3-Amino-1,2,4-benzotriazine-1-N-oxide; 3-amino-1,2,4-benzotriazin-1-ium-1-olate

Database IDs

• CAS Number: 5424-06-6
• MDL Number: MFCD00024038
• PubChem SID: 162070345
• PubChem CID: 79470

CALCULATED PROPERTIES

• Acid pKa: 14.449948
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.30396438
• LogD (pH = 7.4): 0.3039647
• Log P: 0.30396473
• Molar Refractivity: 54.976 cm^3
• Polarizability: 16.788963 Å^3
• Polar Surface Area: 77.26 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate; Methanol (Sparingly)
• Apperance: Yellow Solid
• Melting Point: 270-273°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

MP Biomedicals - 05225021

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - A593640

An intermediate in the synthesis of Tirapazamine, a bioreductive anticancer agent.

REFERENCES

• Delahoussaye, Y., et al.: Biochem. Pharmacol., 62, 1201 (2001)
• Chowdhury, G., et al.: Chem. Res. Toxicol., 17, 1399 (2001)
• Nakashima, H., et al.: Bioorg. Med. Chem., 16, 8661 (2001)