Sodium Azide → Pentanitrophenyl azide

HRID 745743Notes

Reaction equation

HRID 745743 reaction equation
[N+:1]([C:4]1[C:9]([N+:10]([O-])=O)=[C:8]([N+:13]([O-:15])=[O:14])[C:7]([N+:16]([O-:18])=[O:17])=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[N+:22]([O-:24])=[O:23])([O-:3])=[O:2].[N-:25]=[N+:26]=[N-].[Na+]>C1C=CC=CC=1>[N+:1]([C:4]1[C:9]([N:10]=[N+:25]=[N-:26])=[C:8]([N+:13]([O-:15])=[O:14])[C:7]([N+:16]([O-:18])=[O:17])=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[N+:22]([O-:24])=[O:23])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 12488953Hexanitrobenzene

Product 1

HCID 13710295Pentanitrophenyl azide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The reaction is conducted by stirring a benzene solution of hexanitrobenzene with a slight excess of sodium azide (aqueous solution) at 25° C. After separating and drying the benzene solution, the solvent is removed leaving pure pentanitrophenyl azide. Recrystallization from carbon tetrachloride gives either long, flat yellow prisms (α-form) or chunky, orange-yellow rosettes (β-form) of pentanitrophenyl azide.

Workup

  1. customAfter separating
  2. dry with materialdrying the benzene solution
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-fe7221898d2947f88042003349b333f2
Source dataset
uspto-grants-1986_07
Patent number
US04600536

Reaction notes

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