CAS 7598-61-0|diethyl 2,2-diethoxyethylphosphonate|Diethyl(2,2-diethoxyethyl)phosphonate|diethyl (2,2-diethoxyethyl)phosphonate|NSC 77101|NSC 407851|Diethyl 2,2-diethoxyethylphosphonate|Diethyl phos...

General Information

Structure

Molecular Formula

C₁₀H₂₃O₅P

Molecular Mass

254.260381

Exact Mass

254.12831047

Charge

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

Canonic Smiles

CCOC(CP(=O)(OCC)OCC)OCC

Isomeric Smiles

P(=O)(OCC)(OCC)CC(OCC)OCC

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.3012967

LogD (pH = 7.4)

1.3012967

Log P

1.3012967

Molar Refractivity

62.0854

Polarizability

25.289665

Polar Surface Area

53.99

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

Diethyl(2,2-diethoxyethyl)phosphonateNSC 407851Diethyl phosphonoacetaldehyde diethyl acetal2,2-二乙氧基乙基膦酸二乙酯Diethyl 2,2-diethoxyethylphosphonateNSC 77101Diethyl 2,2-DiethoxethylphosphonateP-(2,2-Diethoxyethyl)phosphonic Acid Diethyl EsterDiethylphosphonoacetaldehyde Diethyl Acetal2,2-Diethoxyethylphosphonic acid diethyl esterDiethyl (2,2-Diethoxyethyl)phosphonateDiethyl (2,2-diethoxyethyl)phosphonate2,2-二乙氧基乙基磷酸二乙酯

IUPAC Traditional name

diethyl 2,2-diethoxyethylphosphonate

IUPAC name

diethyl (2,2-diethoxyethyl)phosphonate

Names and Identifiers

Registration numbers

Beilstein Number

1785614

PubChem SID

1620398362489435324858871

PubChem CID

CAS Number

EC Number

MDL Number

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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

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

TRC

D444210

A useful wittig reagent.

Molecule Details

References

PubChem Literature

From Data Sources

• 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):