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

A14433 Ethyl nitroacetate, 97%

Codice CAS
626-35-7
Sinonimi
Nitroacetic acid ethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
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

Proprietà chimiche

Formula
C4H7NO4
Peso formula
133.11
Punto di ebollizione
93-95°/10mm
Punto di infiammabilità
92°(197°F)
Densità
1.202
Indice di rifrazione
1.4240
Solubilità
Slightly soluble in water. Soluble in chloroform and ethyl acetate.

Applicazioni

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.

Note

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

Letteratura

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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H227

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

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
1210027
Codice tariffe armonizzato
2915.90
TSCA
Yes
RTECS
AJ1074000

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