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Chemical Structure| 626-35-7 Chemical Structure| 626-35-7
Chemical Structure| 626-35-7

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Product Citations

Product Citations

Thoenen, Michael ; Scherschel, Nicholas F ; Piercey, Davin G ;

Abstract: Diethyl furoxan dicarboxylate (DFD) is a starting material for fields as diverse as drug discovery, energetics, and any application where a furoxan or furazan may be desired. As with many disubstituted furoxans, they are synthesized via the dimerization of the appropriate nitrile oxide. Past procedures to form DFD involve low-yield destructive nitrations, multiple steps, halogenated solvents, or heavy or precious metals. Although these methods are functional enough for lab-scale preparations of DFD, they do not hold up well for economical scale-up. Our reported procedure improves the synthesis of DFD such that it is available from economical and commercially available starting materials in a single-step, one-pot, high-yield (98.5%) synthesis of material with a trivial workup in high purity (98.2% by 1H quantitative NMR against a 2,4,6-trimethoxy-1,3,5-triazene standard). This improved procedure requires no organic solvents or heavy metals and is the most scalable preparation for this material to date.

Keywords: nitrile oxide ; diethyl furoxan-3,4-dicarboxylate ; esters ; energetic materials

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Product Details of Ethyl nitroacetate

CAS No. :626-35-7
Formula : C4H7NO4
M.W : 133.10
SMILES Code : O=C(OCC)C[N+]([O-])=O
MDL No. :MFCD00007403
InChI Key :FTKASJMIPSSXBP-UHFFFAOYSA-N
Pubchem ID :69379

Safety of Ethyl nitroacetate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H227
Precautionary Statements:P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235

Application In Synthesis of Ethyl nitroacetate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 626-35-7 ]

[ 626-35-7 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 626-35-7 ]
  • [ 54439-75-7 ]
  • (4α,5β)-ethyl 4,6-dichloro-8-oxo-1-oxa-2-azaspiro<4,5>deca-2,6,9-triene-3-carboxylate [ No CAS ]
  • 3
  • [ 626-35-7 ]
  • [ 54439-75-7 ]
  • ethyl (E)-3-(2'-chloro-4'-methoxyphenyl)-2-nitroacrylate [ No CAS ]
  • ethyl (Z)-3-(2'-chloro-4'-methoxyphenyl)-2-nitroacrylate [ No CAS ]
  • 4
  • [ 626-35-7 ]
  • [ 43192-31-0 ]
  • [ 57543-36-9 ]
  • (4α,5β)-ethyl 4,6-dibromo-8-oxo-1-oxa-2-azaspiro<4,5>deca-2,6,9-triene-3-carboxylate [ No CAS ]
  • (4α,5β)-ethyl 4,6,9-tribromo-8-oxo-1-oxa-2-azaspiro<4,5>deca-2,6,9-triene-3-carboxylate [ No CAS ]
  • 5
  • [ 530-48-3 ]
  • [ 626-35-7 ]
  • [ 163520-33-0 ]
  • 6
  • [ 626-35-7 ]
  • [ 287172-82-1 ]
  • [ 122-51-0 ]
  • [ 1422386-57-9 ]
YieldReaction ConditionsOperation in experiment
15% With acetic acid; In ethanol; at 70℃; for 92.0h;Sealed tube; [00395] Intermediate 35A. Ethyl 3-((3-chloro-2,6-difluorophenyl)amino)-2- nitroacrylate: A sealed, high pressure vial containing a clear, colorless solution of ethyl nitroacetate (0.170 ml, 1.529 mmol), triethylorthoformate (0.255 ml, 1.529 mmol), 3- chloro-2,6-difluoroaniline (0.250 g, 1.529 mmol), acetic acid (0.026 ml, 0.459 mmol), and EtOH (1.529 ml) was heated to 70 C. After 92 h, the clear, dark yellow solution was concentrated to give an orange oil. Purification by normal phase chromatography gave Intermediate 35A (0.0721 g, 15%) as a yellow solid. MS(ESI) m/z: 307.0 (M+H)+.
  • 7
  • [ 626-35-7 ]
  • [ 31599-60-7 ]
  • [ 5724-56-1 ]
  • 8
  • [ 626-35-7 ]
  • [ 32566-01-1 ]
  • [ 110059-97-7 ]
 

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