Polyazido compounds

US6841690B1 · kind B1 · utility

Assignee

• The United States of America as represented by the Secretary of the Army · US

Inventors

• Paritosh R. Dave · Little Falls, US
• Raja G. Duddu · Parsippany-Troy Hills, US
• Reddy Damavarapu · Hackettstown, US
• Nathaniel Gelber · Morristown, US
• Kathy Yang · Flanders, US
• C. Rao Surapaneni · Long Valley, US

Key dates

• Filing date: Aug 15, 2003
• Grant date: Jan 11, 2005
• Expiry date: Aug 15, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J41/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention relates to a series of novel compounds having the general structures A and B: including 2-azido-2-azidomethyl-1,3-diazidopropane (1), 2-azidomethyl-2-hydroxy-1,3-diazidopropane (2), 2-azidomethyl-2-nitrato-1,3-diazidopropane (3), 2-azidomethyl-2-nitro-1,3-diazidopropane (4), 2,2-dinitro-1,3-diazidopropane (5), methallyidiazide (6), a dimer of methallyidiazide (6), comprising 3a,8a-Bis-azidomethyl-3a,4,8a,9-tetrahydro-3H,8H-bis[1,2,3]triazolo[1,5-a;1″,5″-d]pyrazine (6-Dimer), 1,3-diazidoacetone (7), and 2-Oximido-1,3-diazidopropane (8). Also shown are reaction intermediates of these compounds, including 2,2-bis(chloromethyl)oxirane (9), and 2,2-bis(azidomethyl)oxirane (10). In addition, a number of potentially useful energetic compounds have been prepared from the low molecular weight polyazido compounds above, including N-2(azido-1-azidomethyl-ethylidene)-N″-(2,4-dinitrophenyl)-hydrazine (7-DNPH), 1,3-Bis(4-carboxytriazolyl)2,2-dinitropropane (12), Tris(4-carboxytriazolomethyl)methanol (13), Benzene-1,3,5-tricarboxylic acid tris(2-azido-1,1-bisazidomethyl-ethyl)ester (14), Adamantane 1,3,5,7-tetracarboxylic acid tetrakis(2-azido-1,1-bisazidomethyl-ethyl)ester (15), A…