Accéder au contenu
Merck
Toutes les photos(1)

Key Documents

View All Documentation

593095

Sigma-Aldrich

Diethyl (2-methylallyl)phosphonate

97%

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule linéaire :
(C2H5O)2POCH2C(=CH2)CH3
Numéro CAS:
51533-70-1
Poids moléculaire :
192.19
Numéro MDL:
MFCD05664300
Code UNSPSC :
12352108
ID de substance PubChem :
24881330
Nomenclature NACRES :
NA.22

Pureté

97%

Capacité de réaction

reaction type: C-C Bond Formation

Indice de réfraction

n20/D 1.4380 (lit.)

Point d'ébullition

62 °C/0.1 mmHg (lit.)

Densité

1.013 g/mL at 25 °C (lit.)

Groupe fonctionnel

phosphonate

Chaîne SMILES 

CCOP(=O)(CC(C)=C)OCC

InChI

1S/C8H17O3P/c1-5-10-12(9,11-6-2)7-8(3)4/h3,5-7H2,1-2,4H3

Clé InChI

QOZGSMHGXZMADD-UHFFFAOYSA-N

Description générale

Diethyl (2-methylallyl)phosphonate is an organophosphorous compound. It participates in the synthesis of α-aminophosphonate derivatives and azaphosphones. The analgesic/antiinflammatory properties of these derivatives were evaluated.

Application

Diethyl (2-methylallyl)phosphonate can be used as a reagent in the Horner-Wadsworth-Emmons reaction to form conjugated carbon–carbon double bonds.
It can also be used as a reactant for:
  • Enantioselective total synthesis of 10-isocyano-4-cadinene as antifouling agent.
  • Regiospecific preparation of 4-oxo-2-alkenylphosphonates (OAP) via silylation followed by Friedel-Crafts acylation and isomerization. OAP can serve as building blocks for the construction of polyethylenic chains.
  • The synthesis of azaphosphone as a potent analgesic/anti-inflammatory agents.

Reactant for:
  • Enantioselective synthesis of 10-isocyano-4-cadinene and its stereoisomers with antifouling activity
  • Preparation of 4-Oxo-2-alkenylphosphonates via silylation followed by regiospecific Friedel-Crafts acylation and isomerization

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Conseils de prudence

P305 + P351 + P338

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

>230.0 °F - closed cup

Point d'éclair (°C)

> 110 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
18431CB

Vous ne trouvez pas la bonne version ?

Si vous avez besoin d'une version particulière, vous pouvez rechercher un certificat spécifique par le numéro de lot.

Rechercher un(e) COA

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Les clients ont également consulté

Slide 1 of 3

1 of 3

Diethyl(3-bromopropyl)phosphonate 95%

Sigma-Aldrich

542032

Diethyl(3-bromopropyl)phosphonate

Vinylphosphonic acid 97%

Sigma-Aldrich

396311

Vinylphosphonic acid

Triethyl phosphite 98%

Sigma-Aldrich

T61204

Triethyl phosphite

Carbodiimides-key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on a-amino-, enaminophosphonates, and azaphosphones.
Abdou WM, et al.
Royal Society of Chemistry Advances, 3(5), 1528-1540 (2013)
I N Smirnova et al.
The journal of physical chemistry. B, 114(50), 16936-16947 (2010-12-01)
The high brilliance of the AILES beamline at the SOLEIL synchrotron facility has been exploited for the study of the gas-phase vibrational spectra of weakly volatile organophosphorous compounds. The propagation of the synchrotron radiation in long path length gas cells
Keisuke Nishikawa et al.
Organic letters, 12(5), 904-907 (2010-02-06)
The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a SmI(2)-induced
Lee et al.
The Journal of organic chemistry, 65(13), 4175-4178 (2000-06-24)
Treatment of allylic and vinylic phosphonates with excess LiHMDS, followed by addition of chlorotrimethylsilane, afforded alpha- and gamma- silylated allylic phosphonate mixtures. Without separation, these mixtures underwent the Friedel-Crafts reaction and base-promoted isomerization to give 4-oxo-2-alkenylphosphonates, which can serve as
(-)-Sparteine-mediated stereoselective intramolecular conjugate addition reactions of dienes and enynes
Oestreich M and Hoppe D
Tetrahedron Letters, 40(10), 1881-1884 (1999)

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique