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

A14433 Ethyl nitroacetate, 97%

Número CAS
626-35-7
Nombre Alternativo
Nitroacetic acid ethyl ester

Tamaño Precio ($) Cantidad Disponibilidad
1g 15,43
5g 59,64
25g 194,10
100g 540,80
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Ethyl nitroacetate, 97%

MDL
MFCD00007403
EINECS
210-944-7

Propiedades químicas

Fórmula
C4H7NO4
Peso molecular
133.11
Punto de ebullición
93-95°/10mm
Punto de inflamabilidad
92°(197°F)
Densidad
1.202
Índice de refracción
1.4240
Solubilidad
Slightly soluble in water. Soluble in chloroform and ethyl acetate.

Aplicaciones

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.

Notas

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

Referencias documentales

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).

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H315-H319-H227

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

Indicaciones de precaución: 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.

Otras referencias

Beilstein
1210027
Código de tarifa arancelaria unificado
2915.90
TSCA
Yes
RTECS
AJ1074000

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