2-methyl-6-phenyl-3H,7H-imidazo[1,2-a]pyrazin-3-one

• ChemBase ID: 153096
• Molecular Formular: C13H11N3O
• Molecular Mass: 225.24594
• Monoisotopic Mass: 225.09021199
• SMILES: Cc1c(=O)n2cc([nH]cc2n1)c1ccccc1
• Canonical SMILES: Cc1nc2n(c1=O)cc([nH]c2)c1ccccc1
• InChI: InChI=1S/C13H11N3O/c1-9-13(17)16-8-11(14-7-12(16)15-9)10-5-3-2-4-6-10/h2-8,14H,1H3
• InChIKey: JYQHFNUMLIRXCQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-6-phenyl-3H,7H-imidazo[1,2-a]pyrazin-3-one
• IUPAC Traditional name: 2-methyl-6-phenyl-7H-imidazo[1,2-a]pyrazin-3-one
• Synonyms: CLA; Cypridina Luciferin analogue; 2-Methyl-6-phenyl-3,7-dihydroimidazo[1,2-a]pyrazin-3(7H)-one

Database IDs

• CAS Number: 19953-58-3
• MDL Number: MFCD00130107
• Beilstein Number: 613436
• PubChem SID: 162247236; 24886999
• PubChem CID: 5158312

CALCULATED PROPERTIES

• Acid pKa: 11.858849
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3132071
• LogD (pH = 7.4): 1.3132052
• Log P: 1.3132198
• Molar Refractivity: 74.77 cm^3
• Polarizability: 24.417114 Å^3
• Polar Surface Area: 44.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (HPLC)
• Grade: for chemiluminescence
• Empirical Formula (Hill Notation): C13H11N3O

DETAILS

Sigma Aldrich - 76489

Other Notes
Generation of chemiluminescence by reaction with superoxide O2- or singlet oxygen1,2