| Identification | More | [Name]
DIFORMYLIMIDE SODIUM SALT | [CAS]
18197-26-7 | [Synonyms]
DIFORMYLAMIDE SODIUM SALT
DIFORMYLIMIDE SODIUM SALT
SODIUM DIFORMAMIDE
SODIUM DIFORMYLAMIDE | [Molecular Formula]
C2H2NNaO2 | [MDL Number]
MFCD00145302 | [Molecular Weight]
95.03 | [MOL File]
18197-26-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Slightly beige powder | [Melting point ]
205°C | [Fp ]
78.9℃ | [storage temp. ]
Inert atmosphere,2-8°C | [Water Solubility ]
Soluble in water | [form ]
Powder | [color ]
Slightly beige | [BRN ]
3567185 | [InChI]
InChI=1S/C2H3NO2.Na/c4-1-3-2-5;/h1-2H,(H,3,4,5);/q;+1/p-1 | [InChIKey]
QJXDSDLNUKLDBP-UHFFFAOYSA-M | [SMILES]
[Na+].[N-](C=O)C=O | [CAS DataBase Reference]
18197-26-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
3-9-34 | [HS Code ]
29251900 |
| Hazard Information | Back Directory | [Chemical Properties]
Slightly beige powder | [Uses]
Reactant for preparation of:
- Functionalized condensed benzazoles
- α-ketoheterocycles as inhibitors of Leishmania mexicana cysteine protease CPB
- INOS inhibitor PHA-399733 via Bucherer-Bergs hydantoin synthesis
- Antibiotic resistance (C β-lactamase AmpC ) inhibitor analogues, with improved cell permeability properties
- BINOL- and H8-BINOL-based aryl phosphites as ligands in palladium-catalyzed asymmetric allylation and amination reactions
- Precursors of αVβ3 integrin antagonists
| [Synthesis]
General procedure for the synthesis of sodium dicarbonylammonium from the compound (CAS: 77287-34-4): formamide (0.35 L, 7.8 mol) was slowly added to a stirred mixture of sodium methanol (0.2 kg, 3.7 mol) and N,N-dimethylformamide (DMF, 1.0 L) at below 50 °C. The reaction mixture was heated to 100 °C and the by-product methanol was collected as a distillate. Subsequently, about 0.3 L of solvent was distilled from the reaction mixture under reduced pressure. After cooling the reaction mixture to 30 °C, the precipitated solid was filtered and washed with DMF (0.2 L). Finally, the solid was dried under vacuum at 75 °C to afford sodium dicarbonylammonium (0.3 kg, 85% yield). | [Purification Methods]
Grind the amide under dry tetrahydrofuran (fumehood), filter and wash it with this solvent, then dry it in vacuo. It is soluble in EtOH and H2O but insoluble in Et2O and pet ether. [IR and preparation: Rakshit J Chem Soc 103 1557 1913, Yinglin & Hongwen Synthesis 122 1990, Allenstein & Beyl Chem Ber 100 355 1967, Allenstein et al. Chem Ber 102 4089 1969, Beilstein 2 II 22.] | [References]
[1] Synthesis, 1990, # 2, p. 122 - 124
[2] Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8723 - 8730
[3] Journal of Organic Chemistry, 2001, vol. 66, # 9, p. 3238 - 3241
[4] Synthetic Communications, 2015, vol. 45, # 16, p. 1864 - 1870 |
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