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339407

Sigma-Aldrich

Ethyl 2-nitropropionate

96%

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About This Item

Linear Formula:
CH3CH(NO2)CO2C2H5
CAS Number:
Molecular Weight:
147.13
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

96%

form

liquid

refractive index

n20/D 1.421 (lit.)

bp

75-76 °C/9 mmHg (lit.)

density

1.13 g/mL at 25 °C (lit.)

functional group

amine
ester
nitro

SMILES string

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

InChI

1S/C5H9NO4/c1-3-10-5(7)4(2)6(8)9/h4H,3H2,1-2H3

InChI key

ZXBGJDZWJJFFQY-UHFFFAOYSA-N

General description

Ethyl 2-nitropropionate is a nitro ester.[1]

Application

Ethyl 2-nitropropionate was used in the preparation of:
  • (−)-trans-2,5-dimethylprolineethyl ester via enantioselective Michael reaction methyl vinyl ketone using modified dihydroquinine as catalyst[2]
  • novel nitrogen-15-labeled nitrone spin trap, 5-ethoxycarbonyl-5-methyl-1-pyrroline N-oxide ([15N]EMPO) for detecting superoxide anion[3]
  • 2-ethoxycarbonyl-2-nitropentanal[1]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

192.2 °F - closed cup

flash_point_c

89 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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5-Carboxy-5-methyl-1-pyrroline N-oxide: a spin trap for the hydroxyl radical.
Tsai P, et al.
J. Chem. Soc. Perkin Trans. II, 6, 875-880 (2001)
H Zhang et al.
FEBS letters, 473(1), 58-62 (2000-05-10)
We describe the synthesis and biological applications of a novel nitrogen-15-labeled nitrone spin trap, 5-ethoxycarbonyl-5-methyl-1-pyrroline N-oxide ([(15)N]EMPO) for detecting superoxide anion. Superoxide anion generated in xanthine/xanthine oxidase (100 nM min(-1)) and NADPH/calcium-calmodulin/nitric oxide synthase systems was readily detected using EMPO
Jeremy R Duvall et al.
The Journal of organic chemistry, 71(22), 8579-8590 (2006-10-27)
The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield.

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