1-methyl 4-pentafluorophenyl 2-(diphenylphosphanyl)benzene-1,4-dicarboxylate

• ChemBase ID: 139804
• Molecular Formular: C27H16F5O4P
• Molecular Mass: 530.379317
• Monoisotopic Mass: 530.07063672
• SMILES: COC(=O)c1ccc(cc1P(c1ccccc1)c1ccccc1)C(=O)Oc1c(c(c(c(c1F)F)F)F)F
• Canonical SMILES: COC(=O)c1ccc(cc1P(c1ccccc1)c1ccccc1)C(=O)Oc1c(F)c(F)c(c(c1F)F)F
• InChI: InChI=1S/C27H16F5O4P/c1-35-27(34)18-13-12-15(26(33)36-25-23(31)21(29)20(28)22(30)24(25)32)14-19(18)37(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-14H,1H3
• InChIKey: OURNVXDJALDDIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl 4-pentafluorophenyl 2-(diphenylphosphanyl)benzene-1,4-dicarboxylate
• IUPAC Traditional name: 1-methyl 4-pentafluorophenyl 2-(diphenylphosphanyl)benzene-1,4-dicarboxylate
• Synonyms: 1-Methyl-4-(pentafluorophenyl)-2-(diphenylphosphino)-1,4-benzenedicarboxylate; 2-(Diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester; 1-甲基-4-(五氟苯基)-2-(二苯基膦)-1,4-苯二羧酸酯; 2-(二苯基膦)对苯二甲酸 1-甲基 4-五氟苯基二酯

Database IDs

• MDL Number: MFCD09265125
• PubChem SID: 162234052; 24885463
• PubChem CID: 16218338

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 7.781
• LogD (pH = 7.4): 7.781
• Log P: 7.781
• Molar Refractivity: 126.5331 cm^3
• Polarizability: 47.37508 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 109-111 °C

Safety Information

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

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C27H16F5O4P

DETAILS

Sigma Aldrich - 679011

Packaging
25, 100 mg in glass bottle
Application

• Staudinger ligation reagent for the conjugation of amine and azide containing compounds or biomolecules.
• The amine functionalized molecule first reacts with the phosphine through the activated pentafluorophenyl ester.The azide-molecule is then reacted with the newly labeled phosphine to form the iminophosphorane, and the aza-ylide is subsequently captured by the methyl ester to yield the covalent conjugated product.1The Staudinger Ligation: A High-Yield, Chemoselective, and Mild Synthetic Method