Consentement d'utilisation des Cookies

J'accepte Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

626-35-7 - Ethyl nitroacetate, 97% - Nitroacetic acid ethyl ester - A14433 - Alfa Aesar

A14433 Ethyl nitroacetate, 97%

Numéro CAS
626-35-7
Synonymes
Nitroacetic acid ethyl ester

Dimensions Prix ($) Quantité Disponibilité
1g 15,43
5g 59,64
25g 194,10
100g 540,80
Ajouter au panier Ajouter au devis en vrac Afficher l'article

Ethyl nitroacetate, 97%

MDL
MFCD00007403
EINECS
210-944-7

Propriétés chimiques

Formule
C4H7NO4
Poids formulaire
133.11
Point d'ébullition
93-95°/10mm
Point d'éclair
92°(197°F)
Densité
1.202
Indice de réfraction
1.4240
Solubilité
Slightly soluble in water. Soluble in chloroform and ethyl acetate.

Applications

Ethyl nitroacetate has been used in the synthesis of γ-oxoacids via Michael addition reaction with α,β-unsaturated ketones, fuctionalization of C4-position on pyrimidine and C6-position on 2?-deoxyguanosine to produce novel nucleosides, facile synthesis of α,α-diisobutylglycine, synthesis of DL-4,4-difluoroglutamic acid. It is also used as an intermediate in the preparation of unsubstituted amino acids.

Notes

Store away from bases and oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Références bibliographiques

Maialen Aginagalde, et al. Formation of γ-oxoacids and 1H-pyrrol-2(5H)-ones from α,β-unsaturated ketones and ethyl nitroacetate.J. Org. Chem.,2010,75(21), 7435-8.

Victor Timoshchuk. Functionalization of pyrimidine and purine nucleosides at C4 and C6: C-nucleophilic substitution of their C4- and C6-(1,2,4-triazol-1-yl) derivatives.Nucleosides Nucleotides Nucleic Acids.,2005,24(5-7), 1043-1046.

In the presence of the Mitsunobu reagent (PPh3/DEAD) oxidizes alcohols to carbonyl compounds: Tetrahedron Lett., 22, 2295 (1981).

Reacts with 2,3-epoxyaldehydes to give 3-ethoxycarbonyl-4-hydroxy-5-(1-hydroxyalkyl)-2-isoxazoline-2-oxides: J. Org. Chem., 55, 781 (1990):

Similarly, reaction with ɑ-bromo enones gives 5-acyl-3-(ethoxycarbonyl)-2-isoxazoline-2-oxides by a tandem conjugate addition - ring closure: J. Org. Chem., 60, 6624 (1995).

Conjugate addition to various enones, followed by reductive cyclization with Formamidinesulfinic acid, A11885, provides a convenient new route to pyrroles: Tetrahedron Lett., 36, 9469 (1995). For examples with reaction schemes, see 2-Benzyl­idenecyclohexanone, L13434 and 3-Penten-2-one, L13031.

For a review of the use of nitroacetic acid and its esters in organic synthesis, see: Synthesis, 666 (1979).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H227

Causes skin irritation. Causes serious eye irritation. Combustible liquid.

Mentions de prudence: P280g-P305+P351+P338

Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Autres références

Beilstein
1210027
Code tarifaire harmonisé
2915.90
TSCA
Yes
RTECS
AJ1074000

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire