ethyl 2-nitroacetate

• ChemBase ID: 9576
• Molecular Formular: C4H7NO4
• Molecular Mass: 133.10268
• Monoisotopic Mass: 133.03750771
• SMILES: C(=O)(C[N+](=O)[O-])OCC
• Canonical SMILES: [O-][N+](=O)CC(=O)OCC
• InChI: InChI=1S/C4H7NO4/c1-2-9-4(6)3-5(7)8/h2-3H2,1H3
• InChIKey: FTKASJMIPSSXBP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-nitroacetate
• IUPAC Traditional name: nitroacetic acid ethyl ester
• Synonyms: Ethyl nitroacetate; Ethyl nitroacetate 97%; Ethyl nitroacetate; 2-Nitroacetic Acid Ethyl Ester; Ethyl 2-Nitroacetate; Ethyl Nitroacetate; NSC 42302; Nitroacetic Acid Ethyl Ester; ethyl 2-nitroacetate; 硝基乙酸乙酯

Database IDs

• CAS Number: 626-35-7
• EC Number: 210-944-7
• MDL Number: MFCD00007403
• Beilstein Number: 1210027
• PubChem SID: 160972883; 24851540; 24886540
• PubChem CID: 69379

CALCULATED PROPERTIES

• Polar Surface Area: 69.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 7.6574793
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.006512483
• LogD (pH = 7.4): -0.18125091
• Log P: 0.009519962
• Molar Refractivity: 27.1857 cm^3
• Polarizability: 10.999308 Å^3

PROPERTIES

Physical Property

• Boiling Point: 105-107 °C/25 mmHg(lit.); 93-95°C/10mm; 93-95°C/10mm
• Flash Point: 197.6 °F; 92 °C; 92°C; 92°C(197°F)
• Density: 1.199; 1.199 g/mL at 25 °C(lit.); 1.202
• Refractive Index: 1.4240; n20/D 1.424; n20/D 1.424(lit.)

Safety Information

• Storage Warning: Irritant; IRRITANT, KEEP COLD
• RTECS: AJ1074000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/38
• Safety Statements: 26-37
• TSCA Listed: true; 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H227
• GHS Precautionary statements: P280G-P305+P351+P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥96.0% (GC); 95+%; 97%
• Grade: purum
• Linear Formula: NO2CH2CO2C2H5

DETAILS

Sigma Aldrich - 192333

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - E925215

Ethyl Nitroacetate is an ester of nitrocarboxylic acid used as an intermediate in the preparation of unsubstituted amino acids.

REFERENCES

• Sidorin, G.I.: Gig. Aspe. Okhr. Zdor. Nasel., 144 (1977)
• In the presence of the Mitsunobu reagent (PPh₃/DEAD) oxidizes alcohols to carbonyl compounds: Tetrahedron Lett., 22, 2295 (1981).
• For a review of the use of nitroacetic acid and its esters in organic synthesis, see: Synthesis, 666 (1979).
• 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.