Microwave assisted facile synthesis of {1/1,3-bis/1,3,5-tris-[(2-nitroxyethylnitramino)-2,4,6-trinitrobenzene]} using bismuth nitrate pentahydrate as an eco-friendly nitrating agent.
1-(2-Nitroxyethylnitramino)-2,4,6-trinitrobenzene (3a), 1,3-bis(2-nitroxyethyl nitramino)-2,4,6-trinitrobenzene (3b) and 1,3,5-tris(2-nitroxyethylnitramino)-2,4,6-trinitrobenzene (3c) were prepared by the nitration of 1-(2-hydroxyethylamino)-2,4,6-trinitrobenzene (2a) 1,3-bis(2-hydroxyethylamino)-2,4,6-trinitrobenzene (2b) and 1,3,5-tris(2-hydroxyethylamino)-2,4,6-trinitrobenzene (2c) using bismuth nitrate pentahydrate (eco-friendly nitrating agent) in tetrahydrofuran adsorbed on silica gel under microwave irradiation, respectively. Key intermediate compounds viz., 2a, 2b and 2c were synthesized by condensing picryl chloride, styphnyl chloride and 1,3,5-trichloro-2,4,6-trinitrobenzene with ethanol amine, respectively, based on the lines of the reported method. The synthesized compounds were characterized based on their physical constant, infrared (IR) spectroscopy and (1)H nuclear magnetic resonance (NMR) spectroscopy. The spectroscopic data obtained indicated the formation of nitrate esters (3a-3c). The nitration methodology adopted in the present study is of relevance in the context of green chemistry. The target compounds (3a-3c) synthesized using eco-friendly approach are of interest from the point of high energy materials (HEMs).
Badgujar
D M
DM
School of Chemical Sciences, North Maharashtra University, Jalgaon, 425001 Maharashtra, India. dmbadgujar@rediffmail.com
Talawar
M B
MB
Asthana
S N
SN
Venugopalan
S
S
Rao
A Subhananda
AS
Mahulikar
P P
PP
D001729:Bismuth; D053834:Explosive Agents / Q000138:chemical synthesis*; D008872:Microwaves; D009566:Nitrates; D014301:Trinitrobenzenes / Q000138:chemical synthesis*
D053834:Explosive Agents; D009566:Nitrates; D014301:Trinitrobenzenes; C065545:bismuth nitrate; D001729:Bismuth