DIFORMYLIMIDE SODIUM SALT Chemical Properties

Melting point:

205°C

Flash point:

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-9-34

HS Code 

29251900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

DIFORMYLIMIDE SODIUM SALT Usage And Synthesis

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

DIFORMYLIMIDE SODIUM SALT(18197-26-7)Related Product Information

• 5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sodium salt
• DIFORMYLIMIDE SODIUM SALT
• Cyanuric acid trisodium salt
• methohexital sodium
• Sodium amide
• Englitazone
• SODIUM PHTHALIMIDE
• Phenytoin sodium
• 6-chloro-1,3,5-triazine-2,4(1H,3H)-dione, sodium salt
• ENGLITAZONE SODIUM
• sodium 5-butyl-5-ethylbarbiturate
• sodium 5-allyl-5-isopropylbarbiturate
• S(-)-Secobarbital sodium
• Azumolene Sodium Salt
• R(+)-Secobarbital sodium
• BIS AZO BARBITURIC ACID SODIUM SALT
• LABOTEST-BB LT00138130
• Sodium isocyanurate