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A12461 Diethyl 2,2-diethoxyethylphosphonate, 96%

CAS Number
7598-61-0
Synonyms
2,2-Diethoxyethylphosphonic acid diethyl ester
Diethyl phosphonoacetaldehyde diethyl acetal

Stock No. Size Price ($) Quantity Availability
A12461-09 10g 87.40
A12461-18 50g 345.00
A12461-30 250g 1399.00
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Diethyl 2,2-diethoxyethylphosphonate, 96%

MDL
MFCD00009236
EINECS
231-504-0

Chemical Properties

Formula
C10H23O5P
Formula Weight
254.26
Boiling Point
101-103°/8mm
Flash Point
>110°(230°F)
Density
1.052
Refractive Index
1.4278
Storage & Sensitivity
Keep Cold. Hygroscopic.
Solubility
Soluble in chloroform and dichloromethane. Not miscible or difficult to mix in water.

Applications

Diethyl 2,2-diethoxyethylphosphonate is used reactant for synthesis of α,β-alkenal derivatives by two-carbon homologation, lower rim-phosphonylated rexorcinol calix[4]arenes by condensation reactions, α-Phosphovinyl radicals via a radical trapping sequence, inhibitors of reverse transcriptase via 1,3-dipolar cycloadditions and for Friedel-Crafts reactions.

Notes

Keep container tightly sealed. It is hygroscopic in nature. It is sensitive to moisture. Store under dry inert gas. Protect from humidity and water.

Literature References

Richard J Petroski.; Karl Vermillion.; Allard A Cossé. Two-carbon homologation of aldehydes and ketones to α,β-unsaturated aldehydes. Molecules. 2011, 16 (6), 5062-5078.

Ugo Chiacchio.; Emanuela Balestrieri.; Beatrice Macchi.; Daniela Iannazzo.; Anna Piperno.; Antonio Rescifina.; Roberto Romeo.; Monica Saglimbeni.; M Teresa Sciortino.; Vincenza Valveri.; Antonio Mastino.; Giovanni Romeo. Synthesis of phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides: novel inhibitors of reverse transcriptase. Journal of Medicinal Chemistry. 2005, 48 (5), 1389-1394.

Wadsworth-Emmons olefination with aldehydes leads to ɑß-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):

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1785614
Harmonized Tariff Code
2931.39
TSCA
No

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