diethyl [(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phosphonate

• ChemBase ID: 74948
• Molecular Formular: C13H16NO5P
• Molecular Mass: 297.243601
• Monoisotopic Mass: 297.07660925
• SMILES: N1(C(=O)c2c(cccc2)C1=O)CP(=O)(OCC)OCC
• Canonical SMILES: CCOP(=O)(CN1C(=O)c2c(C1=O)cccc2)OCC
• InChI: InChI=1S/C13H16NO5P/c1-3-18-20(17,19-4-2)9-14-12(15)10-7-5-6-8-11(10)13(14)16/h5-8H,3-4,9H2,1-2H3
• InChIKey: IUZMHUAHKBHJFY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl [(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phosphonate
• IUPAC Traditional name: diethyl (1,3-dioxoisoindol-2-yl)methylphosphonate
• Synonyms: N-[(Diethoxyphosphoryl)methyl]phthalimide; 2-[(Diethoxyphosphoryl)methyl]-1,3-dioxoisoindoline; Diethyl [(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]phosphonate 98+%; Diethyl (phthalimidomethyl)phosphonate; Phthalimidomethylphosphonic acid diethyl ester; 邻苯二亚胺甲基膦酸二乙酯; (邻苯二酰亚胺甲基)磷酸二乙酯

Database IDs

• CAS Number: 33512-26-4
• MDL Number: MFCD00134313
• PubChem SID: 162039866; 24862629
• PubChem CID: 1924456

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.444983
• LogD (pH = 7.4): 1.444983
• Log P: 1.444983
• Molar Refractivity: 73.25 cm^3
• Polarizability: 28.13269 Å^3
• Polar Surface Area: 72.91 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 60-64 °C(lit.); 60-64°C; 60-64°C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C13H16NO5P

DETAILS

Sigma Aldrich - 366226

Application
Wittig carbonylating reagent.4
Reacant for:
• Horner-Wadsworth-Emmons reactions1
• Preparation of macrocyclic phosphorous acid analogs as inhibitors of HCV-NS3 protease2
• Synthesis of dendrimer-based pH-responsive MRI contrast agent3
Packaging
25 g in poly bottle