3,4-Diaminofurazan Chemical Properties

Melting point:

178-183 °C

Boiling point:

304.0±45.0 °C(Predicted)

Density 

1.582±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

1.31±0.47(Predicted)

form 

Crystalline Powder

color 

White to slightly beige

InChI

InChI=1S/C2H4N4O/c3-1-2(4)6-7-5-1/h(H2,3,5)(H2,4,6)

InChIKey

JHJVSUCUNFXIHN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

17220-38-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

24/25-26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:ACROS

3,4-Diaminofurazan Usage And Synthesis

Description

3,4-Diaminofurazan (DAF) is a simple furanocyclic compound. Since DAF molecule has two highly reactive neighbouring amino groups, it is considered to be the basic structure for the preparation of other complex energetic compounds by oxidation, acylation and azide reactions. Energetic compounds based on DAF include: aminonitrofurazan (ANF), 3,4-dinitrofurazan (DNF), 4,4-diamino-3,3-diazofurazan (DAAF) and 4,4-diamino-3,3-diazofurazan (DAAzF).

Chemical Properties

white to slightly beige crystalline powder

Uses

3,4-Diaminofurazan is a building block used to prepare magnesium and zinc alkynylated salicylaldehyde-diamine Schiff base complexes. 3,4-Diaminofurazan is also used to prepare aryl(hydroxy)oxadiazolopyrazines via oxidation of acetophenones followed by heterocyclization with antibacterial-activities.

Synthesis

The general procedure for the synthesis of 3,4-diaminofurazan from diaminoglyoxime is as follows: Example 1: Synthesis of 3,4-diaminofurazan. In a 500 mL round-bottomed flask equipped with a mechanical stirrer and a thermometer, ethylene glycol (150 mL) was heated to 120 °C. To this hot solution, diaminoglyoxime (50 g, 0.42 mol) and potassium hydroxide (24 g, 0.42 mol) were added sequentially. The reaction mixture was warmed to 170 °C and maintained at this temperature for 1 hour. Upon completion of the reaction, the clarified reaction solution was cooled to room temperature and subsequently slowly poured into a mixture consisting of ice (500 g) and water (100 mL). The mixture was stirred vigorously for 5 minutes until 3,4-diaminofurazan precipitated as solid crystals. The precipitate was collected by filtration, washed with cold water (20 mL) and subsequently dried in air overnight to give 22 g of an off-white solid product (52% yield) with a melting point of 179-181 °C (literature value: Gunasekaran, A. et al., 179-180 °C). The 1H NMR (DMSO-d6) data of the product were as follows: δ 5.81 (s) ppm.

structure and hydrogen bonding

The unit cell parameter for monoclinic crystals of 3,4-Diaminofurazan at 20℃: a = 3.6035(3), b = 11.141(2), c = 10.329(1)Å, β = 94.80(1) , V = 413.2(1)Å3, Z = 4, dcalc = 1.61 g/cm 3, space group C2/c[1]
.

References

[1] A. S. Batsanov, Yu. T. Struchkov. “Crystal structure of 3,4-diaminofurazan and 3-amino-4-nitrofurazan.” Journal of Structural Chemistry 26 1 (1985): 52–56.

3,4-Diaminofurazan(17220-38-1)Related Product Information

• Diaminomaleonitrile
• 1,3-Diaminoguanidine monohydrochloride
• 4,4'-Diaminodiphenylsulfone
• 4,4'-Methylenedianiline
• Dithiooxamide
• Iminodiacetonitrile
• Iminodiacetic acid
• 4-AMINO-5-NITROFURAZANE
• 3,4-Diaminofurazan
• Dimethylaminobenzaldehyde
• 4A,5,9A,10-TETRAHYDRO-4H,9H-[1,2,5]OXADIAZOLO[3,4-B][1,2,5]OXADIAZOLO[3',4':5,6]PYRAZINO[2,3-E]PYRAZINE
• CBI-BB ZERO/003031
• 1-NAPHTHALDEHYDE (4-AMINO-1,2,5-OXADIAZOL-3-YL)HYDRAZONE
• TIMTEC-BB SBB000922
• N,N'-DIISOPROPYL-1,2,5-OXADIAZOLE-3,4-DIAMINE
• TIMTEC-BB SBB000056
• AKOS BB-9481
• [3-(4-AMINO-FURAZAN-3-YL)-5-HYDROXYMETHYL-3H-[1,2,3]TRIAZOL-4-YL]-METHANOL