Ethyl nitroacetate

Base Information

• Chemical Name: Ethyl nitroacetate
• CAS No.: 626-35-7
• Molecular Formula: C4H7NO4
• Molecular Weight: 133.104
• Hs Code.: 29159080
• European Community (EC) Number: 210-944-7
• NSC Number: 42302
• UNII: 7SX8B7W4RD
• DSSTox Substance ID: DTXSID9060817
• Nikkaji Number: J135.425F
• Wikidata: Q72476330
• Mol file: 626-35-7.mol

Synonyms:nitroacetic acid ethyl ester;nitroacetic acid ethyl ester, ammonium salt;nitroacetic acid ethyl ester, ion (1-)

Chemical Property of Ethyl nitroacetate

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 0.212mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 208.565 °C at 760 mmHg
• PKA: pK1:5.85 (25°C)
• Flash Point: 92.222 °C
• PSA: 72.12000
• Density: 1.201 g/cm³
• LogP: 0.34940
• Storage Temp.: Keep Cold
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water. Soluble in chloroform and ethyl acetate.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 133.03750770
• Heavy Atom Count: 9
• Complexity: 116

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl nitroacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 23-24/25-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C[N+](=O)[O-]
• General Description: Ethyl nitroacetate is a versatile reagent that can participate in competitive reactions with electron-deficient olefins, selectively yielding either Michael adducts or isoxazole derivatives depending on reaction conditions. The choice of base strength and the presence of a copper(II) catalyst play a crucial role in directing the reaction pathway, enabling controlled formation of distinct products from this primary nitro compound.

Technology Process of Ethyl nitroacetate

There total 55 articles about Ethyl nitroacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

propylamine (107-10-8,42939-71-9) + diethyl 2-nitro-3-oxopentanedioate (1010117-23-3) → nitroacetic acid ethyl ester (626-35-7) + ethyl 3-propylamino-3-oxopropanoate (71510-96-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1246/bcsj.80.2413

Reference yield: 100.0%

diethyl 2-nitro-3-oxopentanedioate (1010117-23-3) + 4-methoxy-aniline (104-94-9) → nitroacetic acid ethyl ester (626-35-7) + ethyl 3-((4-methoxyphenyl)amino)-3-oxopropanoate (5382-15-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1246/bcsj.80.2413

Reference yield: 99.0%

methanol (67-56-1) + diethyl 2-nitro-3-oxopentanedioate (1010117-23-3) → nitroacetic acid ethyl ester (626-35-7) + ethyl methyl malonate (6186-89-6)

Guidance literature:

In chloroform; at 60 ℃; for 24h;

DOI:10.1246/bcsj.80.2413

upstream raw materials:

ethanol

nitroacetic acid

diethyl nitromalonate

acetic anhydride

Downstream raw materials:

ethyl 3-(1H-indol-3-yl)-2-nitropropanoate

3-benzoylamino-2-nitro-3-phenyl-propionic acid ethyl ester

Ethyl 3-(acetylamino)-2-nitro-3-phenylpropionate

3-ethylamino-3-(4-chloro-phenyl)-2-nitro-propionic acid ethyl ester

Refernces

Michael additions versus cycloaddition condensations with ethyl nitroacetate and electron-deficient olefins

10.1002/chem.200802652

The research study on the competitive reactions between ethyl nitroacetate and electron-deficient olefins under various reaction conditions and catalysts. The purpose of the study was to understand how these reactions could be modulated to favor either Michael additions or cycloaddition-condensations, leading to the formation of either Michael adducts or isoxazole derivatives, respectively. The researchers concluded that the reactions could be selectively steered towards one product or the other by adjusting the strength of the base and the presence of a copper(II) catalyst. Key chemicals used in the process included ethyl nitroacetate as the primary nitro compound, various electron-deficient olefins as dipolarophiles, and bases such as DABCO, DBU, and NMP, as well as copper(II) acetate as a catalyst. The study demonstrated that by manipulating the catalytic system, one could selectively form either Michael adducts or isoxazoline cycloadducts, marking the first report on such selective formation from primary nitro compounds through modulation of the catalytic system.