bis(2,2,2-trifluoroethyl) methylphosphonate

• ChemBase ID: 153031
• Molecular Formular: C5H7F6O3P
• Molecular Mass: 260.0714602
• Monoisotopic Mass: 260.00370003
• SMILES: CP(=O)(OCC(F)(F)F)OCC(F)(F)F
• Canonical SMILES: FC(COP(=O)(OCC(F)(F)F)C)(F)F
• InChI: InChI=1S/C5H7F6O3P/c1-15(12,13-2-4(6,7)8)14-3-5(9,10)11/h2-3H2,1H3
• InChIKey: YIUFTMLPQFZEFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2,2,2-trifluoroethyl) methylphosphonate
• IUPAC Traditional name: bis(2,2,2-trifluoroethyl) methylphosphonate
• Synonyms: Bis(2,2,2-trifluoroethyl) methylphosphonate; 双(2,2,2-三氟乙基)甲基磷酸酯

Database IDs

• CAS Number: 757-95-9
• MDL Number: MFCD00455467
• PubChem SID: 162247171; 24880990
• PubChem CID: 3625610

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7822578
• LogD (pH = 7.4): 1.7822578
• Log P: 1.7822578
• Molar Refractivity: 37.0428 cm^3
• Polarizability: 14.578562 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 24-28 °C(lit.)
• Boiling Point: 183-184 °C(lit.)
• Flash Point: 176 °F; 80 °C
• Refractive Index: n20/D 1.339(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 98%
• Linear Formula: (CF3CH2O)2P(O)CH3

DETAILS

Sigma Aldrich - 579440

Packaging
5, 25 g in glass bottle
Application
Flame-retardant additive for lithium-ion electrolytes1Used as homogenous organic catalytic system2 and as a catalyst for phosphorylation of polyfluoroalkanols3Reactant for:
• Synthesis of fluorescently labeled discodermolide for studying its binding to tubulin4
• Cross metathesis / phosphonate-based intramolecular olefination5
• Olefination for the synthesis of the anticancer microtubule-stabilizing macrolide, (-)-dictyostatin6