Structure of Ethyl nitroacetate
CAS No.: 626-35-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Economic, One-Pot Synthesis of Diethyl Furoxan Dicarboxylate
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.
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Keywords: nitrile oxide ; diethyl furoxan-3,4-dicarboxylate ; esters ; energetic materials
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| 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 |
| 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 |
| Num. heavy atoms | 9 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.75 |
| Num. rotatable bonds | 4 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 30.73 |
| TPSA ? Topological Polar Surface Area: Calculated from |
72.12 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.94 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.48 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.17 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.9 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.55 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.24 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.7 |
| Solubility | 26.3 mg/ml ; 0.198 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.56 |
| Solubility | 3.63 mg/ml ; 0.0273 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.11 |
| Solubility | 102.0 mg/ml ; 0.769 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.77 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.13 |
* 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.

[ 626-35-7 ]
[ 54439-75-7 ]
[ 626-35-7 ]
[ 54439-75-7 ]

[ 626-35-7 ]
[ 43192-31-0 ]
[ 57543-36-9 ]

| Yield | Reaction Conditions | Operation 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)+. |

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