HEAT RESISTANT EXPLOSIVES XV. ALTERNATE SYNTHETIC ROUTES TO 3,3'- DIAMINO-2.2', 4.4', 6.6'-HEXANITROBIPHENYL, DIPAM

3,3'-Diamino-2,2',4,4',6,6'-hexanitrobiphenyl (DIPAM) has been prepared from m-bromoanisole by a new three step synthesis involving the following reactions: m-broonisole to trinitro-m-bromoanisole which was in turn converted to dimethoxy hexanitrobiphenyl via the Ullmann reaction...

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Bibliographic Details
Main Authors: OESTERLING, ROBERT E, DACONS, JOSEPH C, KAPLAN, LLOYD A
Format: Report
Language:English
Subjects:
AMIDES
Ammunition and Explosives
ANILINES
BROMIDES
CHEMICAL REACTIONS
ESTERS
EXPLOSIVES
NITRATES
Organic Chemistry
PHENYL RADICALS
STABILITY
SYNTHESIS
UREIDES
UREIDO
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Summary:3,3'-Diamino-2,2',4,4',6,6'-hexanitrobiphenyl (DIPAM) has been prepared from m-bromoanisole by a new three step synthesis involving the following reactions: m-broonisole to trinitro-m-bromoanisole which was in turn converted to dimethoxy hexanitrobiphenyl via the Ullmann reaction. Conversion of the dimethoxy derivative to DIPAM was readily achieved by treating it with ammonia in alcohol. A second route, starting with m-bromoaniline via the sequence methyl m-bromophenwith m-bromoaniline via the sequence methyl m-bromo- phenylurethane to methyl trinitrom-bromophenyl urethane to the bis-methyl urethane of DIPAM to DIPAM was also attempted because of its simplicity. However, the sole product isolated from thissequence was picramide.