1.3.4.8- Tetranitro-carbazole

Two derivatives of carbazole, 1,3,4,8-tetranitro-carbazole (nirosan, 3) and 1,8-dichloro-3,6-dinitro-carbazole (nirosit, 4) played an important role in the 1940s as insecticides used in vineyards (Pfaff al., 1939 Martin and Shaw, 1946). They are prepared by nitration and chlorination, respectively, of carbazole. 

Preparation of Tetranitro Carbazole , PicArsn Chemical Research Laboratory Rept 136330 (11 April 1951) 7) L. Gowen R, Dwiggens,... 

Polynitro derivatives of monocychc aromatic systems (trinitrobenzene, trinitrotoluene, tetranitro-iV-methylaniline, trinitrophenol, etc.) have long been used as explosives [1]. It has been found that a series of polynitroderivatives of biphenyl, diphenylmethane and 1,2-diphenylethylene (stilbene) are explosives liable to detonate on grinding or impact [2]. The same may be true of other polynitro derivatives of polycyclic systems not normally used as explosives (e.g. polynitro-fluorenones, -carbazoles, etc. Penta- and hexa-nitrobenzophenones are also high-energy explosives [3]. The thermal stability of 33 polynitroaromatics was studied by DTA [4]. Two empirical equations relating the heat of decomposition to the heat of detonation have been developed and used to calculate the heats of detonation for 47 polynitroaryl compoimds [5]. 

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