(3E)-3-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]butan-2-one

• ChemBase ID: 166940
• Molecular Formular: C10H10N4O5
• Molecular Mass: 266.2102
• Monoisotopic Mass: 266.06511944
• SMILES: c1c(ccc(c1[N+](=O)[O-])N/N=C(/C(=O)C)\C)[N+](=O)[O-]
• Canonical SMILES: CC(=O)/C(=N/Nc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])/C
• InChI: InChI=1S/C10H10N4O5/c1-6(7(2)15)11-12-9-4-3-8(13(16)17)5-10(9)14(18)19/h3-5,12H,1-2H3/b11-6+
• InChIKey: CMMZDRNKABQCMK-IZZDOVSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-3-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]butan-2-one
• IUPAC Traditional name: (3E)-3-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]butan-2-one
• Synonyms: 2-[2-(2,4-Dinitrophenyl)hydrazone] 2,3-Butanedione; Mono[(2,4-dinitrophenyl)hydrazone] 2,3-Butanedione; Diacetyl 2,4-Dinitrophenylhydrazone

Database IDs

• CAS Number: 2256-00-0
• PubChem SID: 162261073
• PubChem CID: 9568776

CALCULATED PROPERTIES

• Acid pKa: 8.50531
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 3.0399058
• LogD (pH = 7.4): 3.0081391
• Log P: 3.0403326
• Molar Refractivity: 67.9279 cm^3
• Polarizability: 23.571678 Å^3
• Polar Surface Area: 133.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D422550

2,4-Dinitrophenylhydrazone (DNPH) derivative. Also, it is used in TLC as internal standards.

REFERENCES

• Lindsay, R.C., et al.: J. Food Sci., 29, 266 (1964)