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

A14433 Ethyl nitroacetate, 97%

CAS Number
626-35-7
Synonyms
Nitroacetic acid ethyl ester

Size Price ($) Quantity Availability
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

Chemical Properties

Formula
C4H7NO4
Formula Weight
133.11
Boiling Point
93-95°/10mm
Flash Point
92°(197°F)
Density
1.202
Refractive Index
1.4240
Solubility
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.

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H227

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

Precautionary Statements: 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.

Other References

Beilstein
1210027
Harmonized Tariff Code
2915.90
TSCA
Yes
RTECS
AJ1074000

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