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192333

Sigma-Aldrich

Ethyl nitroacetate

97%

Sinonimo/i:

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

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About This Item

Formula condensata:
NO2CH2CO2C2H5
Numero CAS:
626-35-7
Peso molecolare:
133.10
Beilstein:
1210027
Numero CE:
210-944-7
Numero MDL:
MFCD00007403
Codice UNSPSC:
12352100
ID PubChem:
24851540
NACRES:
NA.22

Saggio

97%

Indice di rifrazione

n20/D 1.424 (lit.)

P. ebollizione

105-107 °C/25 mmHg (lit.)

Densità

1.199 g/mL at 25 °C (lit.)

Gruppo funzionale

amine
ester
nitro

Stringa SMILE

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

InChI

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

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Applicazioni

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

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

197.6 °F - closed cup

Punto d’infiammabilità (°C)

92 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
BCCF8356
BCCC7550
BCBZ3215
BCBW6088
BCBP1661V

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T Tsukamoto et al.
Journal of medicinal chemistry, 39(1), 66-72 (1996-01-05)
DL-4,4-Difluoroglutamic acid (DL-4,4-F2Glu) and its methotrexate analogue, DL-gamma,gamma-difluoromethotrexate (DL-gamma,gamma-F2MTX), were synthesized and evaluated as alternate substrates or inhibitors of folate-dependent enzymes. Synthesis of DL-4,4-F2Glu involved the nitroaldol reaction of ethyl nitroacetate with a difluorinated aldehyde ethyl hemiacetal as a key
Indranil Bhattacharjee et al.
Physical chemistry chemical physics : PCCP, 20(9), 6060-6072 (2017-12-23)
Achieving synthetic control over light-driven molecular dynamics is essential for designing complex molecule-based devices. Here we design a novel coumarin-imidazole conjugate (1) whose excited state structural dynamics are primarily controlled by a distant intramolecular H-bonding interaction within the backbone. The
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
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