ethyl 2-[bis(propan-2-yloxy)phosphoryl]acetate

• ChemBase ID: 150576
• Molecular Formular: C10H21O5P
• Molecular Mass: 252.244501
• Monoisotopic Mass: 252.1126604
• SMILES: CCOC(=O)CP(=O)(OC(C)C)OC(C)C
• Canonical SMILES: CCOC(=O)CP(=O)(OC(C)C)OC(C)C
• InChI: InChI=1S/C10H21O5P/c1-6-13-10(11)7-16(12,14-8(2)3)15-9(4)5/h8-9H,6-7H2,1-5H3
• InChIKey: YZEWJYIDAAGEHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-[bis(propan-2-yloxy)phosphoryl]acetate
• IUPAC Traditional name: ethyl 2-(diisopropoxyphosphoryl)acetate
• Synonyms: Ethyl (diisopropyl phosphono)acetate; Diisopropyl (ethoxycarbonylmethyl)phosphonate; 二异丙基(乙氧基羰甲基)磷酸酯

Database IDs

• CAS Number: 24074-26-8
• MDL Number: MFCD00075267
• PubChem SID: 162244737; 24861175
• PubChem CID: 1800506

CALCULATED PROPERTIES

• Acid pKa: 17.37997
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4475818
• LogD (pH = 7.4): 1.4475818
• Log P: 1.4475818
• Molar Refractivity: 60.4511 cm^3
• Polarizability: 24.684145 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 142-143 °C/11 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.06 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.427(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%
• Linear Formula: C2H5O2CCH2P(O)[OCH(CH3)2]2

DETAILS

Sigma Aldrich - 343560

Packaging
5 g in glass bottle
Application
Reactant for:
• Preparation of spiroimine ring fragment of spirolides via stereoselective intermolecular Diels-Alder and aza-Wittig cyclization1
• Katsuki-Sharpless epoxidation reaction2
• Preparation of nine-membered diallylic sulfonamides as chiral building blocks3
• Alpha-phosphono lactams for subsequent Wadsworth-Emmons olefination, and Suzuki coupling reactions to yield diverse pyrrolidinone compounds4
• Synthesis of galactosylceramide analog that induces Th1-biased responses in human (NKT) cells5
• Stereoselective total synthesis of the ionophore antibiotic zincophorin (M144255)6