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192333

Sigma-Aldrich

Ethyl nitroacetate

97%

Synonym(s):

2-Nitroacetic acid ethyl ester, Ethyl 2-nitroacetate, Nitroacetic acid ethyl ester

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About This Item

Linear Formula:
NO2CH2CO2C2H5
CAS Number:
626-35-7
Molecular Weight:
133.10
Beilstein:
1210027
EC Number:
210-944-7
MDL number:
MFCD00007403
UNSPSC Code:
12352100
PubChem Substance ID:
24851540
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.424 (lit.)

bp

105-107 °C/25 mmHg (lit.)

density

1.199 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C[N+]([O-])=O

InChI

1S/C4H7NO4/c1-2-9-4(6)3-5(7)8/h2-3H2,1H3

InChI key

FTKASJMIPSSXBP-UHFFFAOYSA-N

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Application

Ethyl nitroacetate has been used in:
  • 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

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

197.6 °F - closed cup

Flash Point(C)

92 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yanwen Fu et al.
The Journal of organic chemistry, 68(25), 9854-9857 (2003-12-06)
alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N(alpha)-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are
Elena Trogu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(7), 2081-2093 (2012-01-12)
Base-catalysed condensation reactions of nitroacetic esters with dipolarophiles to give isoxazole derivatives proceed faster, and often with higher yields, in the presence of water than in organic solvents such as chloroform. Kinetic profiles show that induction times are greatly reduced
Maialen Aginagalde et al.
The Journal of organic chemistry, 75(21), 7435-7438 (2010-10-05)
Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus
Victor Timoshchuk
Nucleosides, nucleotides & nucleic acids, 24(5-7), 1043-1046 (2005-10-27)
A study of C-nucleophilic substitution at the C4-position on pyrimidine and C6-position on 2'-deoxyguanosine to produce novel nucleosides is presented with the spectroscopic properties of their respective substitution products. C4-(1,2,4-triazol-1-yl) pyrimidine nucleosides 1 were treated with nitroalkanes, malononitrile, acetylacetone, ethyl
Elena Trogu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(32), 7940-7948 (2009-04-24)
Ethyl nitroacetate (1) reacts with electron-poor olefins in the presence of a base to give either the Michael adducts 3 or the isoxazoline cycloadducts 4, resulting from water elimination. The proportions of the two products depend on the reaction conditions
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