3-Aminofurazan-4-carboxylic acid Chemical Properties

Melting point:

216-217 °C(Solv: water (7732-18-5))

Boiling point:

385.4±52.0 °C(Predicted)

Density 

1.756±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

3.40±0.10(Predicted)

Appearance

Light brown to off-white Solid

InChI

InChI=1S/C3H3N3O3/c4-2-1(3(7)8)5-9-6-2/h(H2,4,6)(H,7,8)

InChIKey

YOXIXLVJYMCCIB-UHFFFAOYSA-N

SMILES

O1N=C(N)C(C(O)=O)=N1

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2934999090

3-Aminofurazan-4-carboxylic acid Usage And Synthesis

Uses

3-Aminofuran-4-carboxylic acid is a carboxylic acid organic compound and an important intermediate in the synthesis of compounds such as furazan, oxyfuran, and pyrrolifuran.

Synthesis

To a stirred suspension of ethyl cyanoacetate (28.3 g, 0.25 mol, 1.0 eq.) and sodium nitrite (17.3 g, 0.25 mol, 1.0 eq.) in a mixture of ethanol (17 mL) and water (200 mL) was added 85% phosphoric acid (10 mL) slowly and dropwise at 10-15°C with continuous stirring for 12 hours. Upon completion of the reaction, the reaction mixture was treated sequentially with sodium hydroxide (4 x 10 g, 1 mol, 4.0 eq.) and potassium hydroxide (2 x 14 g, 0.5 mol, 2.0 eq.). Hydroxylamine hydrochloride (NH2OH-HCl, 69.5 g, 1.0 mol, 4.0 eq.) was slowly added to the resulting solution at room temperature, followed by heating the reaction mixture to 95 °C and stirring for 2 hours. After completion of the reaction, it was cooled to room temperature and quenched with concentrated hydrochloric acid. The mixture was cooled to 0 °C and allowed to stand for 12 h to precipitate, the precipitate was collected by filtration and dried. The filtrate was extracted with ether (3 x 30 mL), the organic phases were combined and concentrated under reduced pressure. The concentrated residue was combined with the previously obtained precipitate and recrystallized from hot water to afford the target compound 4-amino-1,2,5-oxadiazole-3-carboxylic acid (21.3 g, 0.165 mol, 66% yield) as a white solid. The product was characterized by 1H-NMR (300 MHz, DMSO-d6), 13C-NMR (75 MHz, DMSO-d6) and HRMS (ESI), and the data were consistent with the expected structure.

References

[1] Patent: EP3305783, 2018, A1. Location in patent: Paragraph 0092; 0093

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