2,5-dioxopyrrolidin-1-yl diphenyl phosphate

• ChemBase ID: 137219
• Molecular Formular: C16H14NO6P
• Molecular Mass: 347.259221
• Monoisotopic Mass: 347.0558738
• SMILES: c1ccc(cc1)OP(=O)(Oc1ccccc1)ON1C(=O)CCC1=O
• Canonical SMILES: O=C1CCC(=O)N1OP(=O)(Oc1ccccc1)Oc1ccccc1
• InChI: InChI=1S/C16H14NO6P/c18-15-11-12-16(19)17(15)23-24(20,21-13-7-3-1-4-8-13)22-14-9-5-2-6-10-14/h1-10H,11-12H2
• InChIKey: BXMVKQIIJSXIBU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl diphenyl phosphate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl diphenyl phosphate
• Synonyms: SDPP; Diphenyl N-succinimidyl phosphate; 二苯基 N-琥珀酰亚胺磷酸酯

Database IDs

• CAS Number: 75513-55-2
• MDL Number: MFCD00274258
• PubChem SID: 162231484
• PubChem CID: 4386397

CALCULATED PROPERTIES

• Acid pKa: 17.567719
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.6533866
• LogD (pH = 7.4): 2.6533866
• Log P: 2.6533866
• Molar Refractivity: 83.4387 cm^3
• Polarizability: 33.254513 Å^3
• Polar Surface Area: 82.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 83-86 °C(lit.)

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (CHN); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C16H14NO6P

DETAILS

Sigma Aldrich - 43310

Other Notes
Reactive reagent to prepare N-succinimidyl esters from acids1; Peptide coupling reagent giving some racemization2