Organic Chemistry of Explosives

6-Membered rings – 4N 321

Agrawal and co-workers^122 synthesized the insensitive triazine-based explosive PL-1 (193)

from the reaction of cyanuric chloride (191) with 3,5-dichloroaniline (192), followed by ni-

tration and displacement of the chloro groups with ammonia in acetone. PL-1 (193) (VOD∼

7861 m/s,d= 2 .02 g/cm^3 , DTA exotherm at 335◦C) has overall comprehensive properties

close to TATB.

N

N

194

N

NO 2

O 2 N NO 2

Figure 7.72

2,4,6-Trinitro-1,3,5-triazine (194) has seen numerous attempts^123 at its synthesis, but it

remains elusive and is probably too unstable for isolation under normal conditions.

7.9 6-Membered rings – 4N

H 2 NHN NHNH2.HCl

N

NH 2

NN

NN

N

N

N

N

CH 3

H 3 C

H 3 C

CH 3

N

NN

N

NH 2

NH 2

198

H 2 N NHNH2.HCl

N

NH 2

N

NNH

NH

NH2.HCl

NH 2

200

NaBO 3

N

NNH

NH

N

N

N

N

CH 3

H 3 C

H 3 C

CH 3

CH 3 COCH 2 COCH 3

CH 3 COCH 2 COCH 3

195

199

197

NH 3 , NMP,

90 °C

NO or NO 2

196

Figure 7.73

Tetrazine-based explosives are often highly energetic. The high nitrogen content of such

compounds often results in high crystal density and explosive performance. 3,6-Diamino-

1,2,4,5-tetrazine (198) is a starting material for the synthesis of other 1,2,4,5-tetrazines

and is itself synthesized from the condensation of triaminoguanidine hydrochloride (195)