diethyl [(diethoxyphosphoryl)methyl]phosphonate

• ChemBase ID: 75008
• Molecular Formular: C9H22O6P2
• Molecular Mass: 288.214902
• Monoisotopic Mass: 288.08916168
• SMILES: P(=O)(CP(=O)(OCC)OCC)(OCC)OCC
• Canonical SMILES: CCOP(=O)(CP(=O)(OCC)OCC)OCC
• InChI: InChI=1S/C9H22O6P2/c1-5-12-16(10,13-6-2)9-17(11,14-7-3)15-8-4/h5-9H2,1-4H3
• InChIKey: STJWVOQLJPNAQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl [(diethoxyphosphoryl)methyl]phosphonate
• IUPAC Traditional name: diethyl (diethoxyphosphoryl)methylphosphonate
• Synonyms: NSC 133889; Bis(diethoxyphosphinyl)methane; Methylenediphosphonic acid tetraethylester; Tetraethyl methylenediphosphonate; Tetraethyl methanediylbis(phosphonate); Tetraethyl (methylene)bisphosphonate; Methylenediphosphonic acid tetraethyl ester; 亚甲基二磷酸四乙酯; 双(二乙氧基氧膦基)甲烷; 四乙基亚甲基二磷酸酯; 亚甲基二磷酸四乙酯

Database IDs

• CAS Number: 1660-94-2
• EC Number: 216-764-5
• MDL Number: MFCD00039887
• Beilstein Number: 1813241
• PubChem SID: 162039926; 24862057
• PubChem CID: 15455

CALCULATED PROPERTIES

• Polarizability: 26.840658 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2342206
• LogD (pH = 7.4): 1.2342206
• Log P: 1.2342206
• Molar Refractivity: 64.8021 cm^3

PROPERTIES

Physical Property

• Boiling Point: 151-153°C/1.2mm; 171-174 °C/11 mmHg(lit.); 171-174°C
• Flash Point: >110°C; >110°C(230°F); 110 °C; 230 °F
• Density: 1.16 g/mL at 25 °C(lit.); 1.162
• Refractive Index: 1.4400; n20/D 1.442; n20/D 1.442(lit.)

Safety Information

• Storage Warning: Irritant
• RTECS: SZ9150000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-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: ≥97.0% (GC); 97%; 98+%
• Grade: purum
• Linear Formula: CH2[P(O)(OCH2CH3)2]2

DETAILS

Sigma Aldrich - 359181

Packaging
5, 25 mL in glass bottle
Application
Reactant for synthesis of:
• Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase1
• Unnatural alpha-amino acid derivatives containing gem-biphosphonates2
• Biphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption3
• Lycopene via Wittig-Horner reaction4
• Alkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthase5
• Aromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthase6Precursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition7

Sigma Aldrich - 64256

Other Notes
Horner-Wittig reagent for the synthesis of vinylic phosphonates 8; Preparation of isosters of phosphates by Horner- Wittig reaction followed by hydrogenation 9,10
Application
Reactant for synthesis of:
• Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase1
• Unnatural alpha-amino acid derivatives containing gem-biphosphonates2
• Biphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorption3
• Lycopene via Wittig-Horner reaction4
• Alkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthase5
• Aromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthase6Precursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition7

REFERENCES

• Reacts with aromatic aldehydes to give styrylphosphonates in a two-phase system, no added phase-transfer catalyst being necessary: Synthesis, 396 (1976). For cleavage of the resulting vinyl phosphonates to ɑ-hydroxyaldehydes, see Osmium(VIII) oxide, 12103.