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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%

Numéro CAS
7598-61-0
Synonymes
2,2-Diethoxyethylphosphonic acid diethyl ester
Diethyl phosphonoacetaldehyde diethyl acetal

Dimensions Prix ($) Quantité Disponibilité
10g 84,40
50g 338,00
250g 1371,00
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Diethyl 2,2-diethoxyethylphosphonate, 96%

MDL
MFCD00009236
EINECS
231-504-0

Propriétés chimiques

Formule
C10H23O5P
Poids formulaire
254.26
Point d'ébullition
101-103°/8mm
Point d'éclair
>110°(230°F)
Densité
1.052
Indice de réfraction
1.4278
Sensibilité
Moisture Sensitive
Solubilité
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.

Références bibliographiques

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):

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319

Causes skin irritation. Causes serious eye irritation.

Mentions de prudence: 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.

Autres références

Beilstein
1785614
Code tarifaire harmonisé
2931.90
TSCA
No

Recommandé

  • A10967

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

    Bromoacetaldehyde diethyl acetal, 97%
  • A14427

    Indole, 99%
  • 33369

    Sodium hypochlorite, 11-15% available chlorine

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