Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

7598-61-0 - Diethyl 2,2-diethoxyethylphosphonate, 96% - 2,2-Diethoxyethylphosphonic acid diethyl ester - Diethyl phosphonoacetaldehyde diethyl acetal - A12461 - Alfa Aesar

A12461 Diethyl 2,2-diethoxyethylphosphonate, 96%

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

Size Price ($) Quantity Availability
10g 85.18
50g 268.00
250g 1075.20
Add to Cart Add to Quote Request View Item

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
Sensitivity
Moisture Sensitive
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

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280-P264-P305+P351+P338-P362-P321-P332+P313-P337+P313-P302+P352

Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Take off contaminated clothing and wash before reuse. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: IF ON SKIN: Wash with plenty of soap and water.

Other References

Beilstein
1785614
Harmonized Tariff Code
2931.90
TSCA
No

Recommended

  • A10967

    (R)-(+)-1-Phenylethylamine, 98%
  • A13276

    Bromoacetaldehyde diethyl acetal, 97%
  • A14427

    Indole, 99%
  • 33369

    Sodium hypochlorite, 11-15% available chlorine

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware