diethyl (2,2-diethoxyethyl)phosphonate

• ChemBase ID: 74918
• Molecular Formular: C10H23O5P
• Molecular Mass: 254.260381
• Monoisotopic Mass: 254.12831047
• SMILES: P(=O)(OCC)(OCC)CC(OCC)OCC
• Canonical SMILES: CCOC(CP(=O)(OCC)OCC)OCC
• InChI: InChI=1S/C10H23O5P/c1-5-12-10(13-6-2)9-16(11,14-7-3)15-8-4/h10H,5-9H2,1-4H3
• InChIKey: LUQYELQXRPNKRY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (2,2-diethoxyethyl)phosphonate
• IUPAC Traditional name: diethyl 2,2-diethoxyethylphosphonate
• Synonyms: Diethyl(2,2-diethoxyethyl)phosphonate; Diethyl phosphonoacetaldehyde diethyl acetal; NSC 407851; NSC 77101; Diethyl 2,2-diethoxyethylphosphonate; Diethyl (2,2-diethoxyethyl)phosphonate; 2,2-Diethoxyethylphosphonic acid diethyl ester; P-(2,2-Diethoxyethyl)phosphonic Acid Diethyl Ester; Diethyl (2,2-Diethoxyethyl)phosphonate; Diethylphosphonoacetaldehyde Diethyl Acetal; Diethyl 2,2-Diethoxethylphosphonate; 2,2-二乙氧基乙基膦酸二乙酯; 2,2-二乙氧基乙基磷酸二乙酯

Database IDs

• CAS Number: 7598-61-0
• EC Number: 231-504-0
• MDL Number: MFCD00009236
• Beilstein Number: 1785614
• PubChem SID: 24894353; 24858871; 162039836
• PubChem CID: 82071

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.3012967
• LogD (pH = 7.4): 1.3012967
• Log P: 1.3012967
• Molar Refractivity: 62.0854 cm^3
• Polarizability: 25.289665 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Colourless Oil
• Boiling Point: 101-103°C @0.8mm; 101-103°C/8mm; 146-149 °C/14 mmHg(lit.)
• Flash Point: >110°C(230°F); 110 °C; 230 °F
• Density: 1.052; 1.052 g/mL at 25 °C(lit.)
• Refractive Index: 1.4278; n20/D 1.430; n20/D 1.430(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (GC); 95%; 95+%; 96%
• Grade: technical
• Linear Formula: (CH3CH2O)2CHCH2P(O)(OCH2CH3)2

DETAILS

Sigma Aldrich - D99250

Packaging
5, 25 g in glass bottle
Application
Reactant for synthesis of:
• α,β-Alkenal derivatives by two-carbon homologation1
• Lower rim-phosphonylated rexorcinol calix[4]arenes by condensation reactions2,3
• α-Phosphovinyl radicals via a radical trapping sequence4
• Inhibitors of reverse transcriptase via 1,3-dipolar cycloadditions5Reactant for Friedel-Crafts reactions6

Sigma Aldrich - 31610

Other Notes
Stable precursor to (formylmethyl)phosphonate7,8
Application
Reactant for synthesis of:
• α,β-Alkenal derivatives by two-carbon homologation1
• Lower rim-phosphonylated rexorcinol calix[4]arenes by condensation reactions2,3
• α-Phosphovinyl radicals via a radical trapping sequence4
• Inhibitors of reverse transcriptase via 1,3-dipolar cycloadditions5Reactant for Friedel-Crafts reactions6

Toronto Research Chemicals - D444210

A useful wittig reagent.

REFERENCES

• Wadsworth-Emmons olefination with aldehydes leads to ɑ?-enals: Bull. Chem. Soc. Jpn., 30, 1498 (1962). This reaction fails for ketones since the ylide loses EtO^-. This can be avoided by prior conversion of the acetal to the corresponding cyclohexyl enamine: Org. Synth. Coll., 6, 448 (1988), followed by reaction with the ketone: Org. Synth. Coll., 6, 358 (1988):