3,5-dinitro-1H-1,2,4-triazole → sodium tetrakis(3,5-dinitro-1H-1,2,4-triazolyl)borate

HRID 627295

Reaction equation

[N+:1]([C:4]1[N:8]=[C:7]([N+:9]([O-:11])=[O:10])[NH:6][N:5]=1)([O-:3])=[O:2].[BH4-:12].[Na+:13].[H][H]>COCCOCCOC>[N+:1]([C:4]1[N:8]=[C:7]([N+:9]([O-:11])=[O:10])[N:6]([B-:12]([N:5]2[C:4]([N+:1]([O-:3])=[O:2])=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[N:6]2)([N:5]2[C:4]([N+:1]([O-:3])=[O:2])=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[N:6]2)[N:5]2[C:4]([N+:1]([O-:3])=[O:2])=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[N:6]2)[N:5]=1)([O-:3])=[O:2].[Na+:13]

Participants

Conditions

Temperature: 50 °C

Procedure

Under anhydrous conditions and a stream of dry nitrogen, 6.36 g (40.0 mmol) 3,5-dinitro-1H-1,2,4-triazole and 37.8 mg (10.0 mmol) sodium borohydride were loaded into a dry 250 mL three-necked round bottom flask that was equipped with a TEFLON™ coated stirring bar, an addition funnel and a reflux condenser. While stirring, 50 mL of anhydrous 1-methoxy-2-(2-methoxyethoxy)ethane (diglyme) was carefully added through the addition funnel. Immediately, hydrogen gas was evolved and the reaction mixture turned yellow-orange. When the addition was complete, the addition funnel was replaced by a stopper. The mixture was heated to 50° C. for three hours and then to 110° C. for an additional 24 hours. The obtained orange solution was allowed to cool to ambient temperature and all volatiles were pumped-off in vacuo. Subsequent evacuation to a constant weight over a period of 48 hours resulted in a yellow solid of sodium tetrakis(3,5-dinitro-1H-1,2,4-triazolyl)borate, 8.5 g. Decomposition temperature: 167.6° C. (TGA, weight loss: 69.4%), density: 1.80 g/cm3 at 20° C.

Workup

additionWhen the addition
temperatureto cool to ambient temperature

Sources & evidence

ORD record: ord-29b5eb4f4eaf492895480b444328247c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309266B2

Linked notes

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