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7598-61-0 molecular structure
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diethyl (2,2-diethoxyethyl)phosphonate

ChemBase ID: 74918
Molecular Formular: C10H23O5P
Molecular Mass: 254.260381
Monoisotopic Mass: 254.12831047
SMILES and InChIs

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

Cite this record

CBID:74918 http://www.chembase.cn/molecule-74918.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

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 cm3
Polarizability 25.289665 Å3 Polar Surface Area 53.99 Å2
Rotatable Bonds 10  Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Apperance
Colourless Oil expand Show data source
Boiling Point
101-103°C @0.8mm expand Show data source
101-103°C/8mm expand Show data source
146-149 °C/14 mmHg(lit.) expand Show data source
Flash Point
>110°C(230°F) expand Show data source
110 °C expand Show data source
230 °F expand Show data source
Density
1.052 expand Show data source
1.052 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4278 expand Show data source
n20/D 1.430 expand Show data source
n20/D 1.430(lit.) expand Show data source
Storage Warning
Moisture Sensitive expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
36/38 expand Show data source
Safety Statements
26-37 expand Show data source
26-37/39 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P280-P305+P351+P338-P302+P352-P321-P362-P332+P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95% (GC) expand Show data source
95% expand Show data source
95+% expand Show data source
96% expand Show data source
Grade
technical expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
(CH3CH2O)2CHCH2P(O)(OCH2CH3)2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - D99250 external link
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 external link
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 external link
A useful wittig reagent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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):
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PATENTS

PATENTS

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INTERNET

INTERNET

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