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Synthesis of CL-18

CL-18, a code name for aminonitrobenzodifuroxan, is an insensitive high explosive compound of recent development. This compound belongs to a class of molecules that is extremely dense; a high density is a prized feature of modern explosives. CL-18 is also classified as an insensitive munition, being resistant to impact, friction, and electric shock. CL-18 is still in the experimental stages, but is being evaluated for a variety of military purposes. If CL-18 is as promising as its developers hope, it will likely replace whatever application TATB or RDX is currently being used for.


CxHyOz
b.p. ? °C mass ? g/mol
m.p. 205 °C CAS# 83454-00-6
den. 1.93 g/mL v.det. 8370 m/s

4-amino-5-nitrobenzo[1,2-c:3,4-c’]bis[1,2,5]oxadiazole-3,8-dioxide
7-amino-6-nitrobenzodifuroxan
aminonitrobenzodifuroxan
ANBDF
benzo[1,2-c:3,4-c']bis[1,2,5]oxadiazol-4-amine, 5-nitro-, 3,8-dioxide (9CI)


CL-18

CL-18

Synthesis 1:
Prepare a solution of 2.0 g of pentanitroaniline dissolved in 20 mL of room temperature acetic acid.  Slowly add 1.63 g of sodium azide, with stirring, in small portions while keeping the temperature below 32 C.  Stir the solution for 15 minutes at 25 C, and then heat the solution on a water bath at 80 C for 1 hour while stirring.  Stop heating and let the solution sit at room temperature for 12-16 hours to allow for complete precipitation of the product.  Filter to collect the yellow precipitate, wash it with two 25 mL portions of water, and allow to dry.  Final yield is nearly 1.2 g or 73%.

Synthesis 2:
Prepare a solution of 5.0 g of pentanitroaniline dissolved in 800 mL of room temperature dichloroethane.  Prepare a second solution of 2.14 g of sodium azide in 50 mL of water.  Slowly add the azide solution dropwise to the pentanitroaniline solution while keeping the temperature below 30 C.  Stir the mixture for 1 hour at room temperature.  Stop stirring and allow the immiscible layers to form, collect the dichloroethane layer and place it in an Erlenmeyer flask. Dry the solvent by adding several grams of anhydrous magnesium sulfate and stirring for 2 hours.  Filter to remove the magnesium sulfate, and then place the filtrate in a round-bottomed flask.  Reflux the filtrate for 90 minutes, and then allow it to cool to room temperature.  While cooling a yellow precipitate should form, filter to collect this material, wash it with one portion of 50 mL of dichloroethane, and allow to dry in the open air.  Final yield of CL-18 is a little over 2.3 g or 58%.

While a good faith effort has been made to ensure the accuracy of all scientific information presented on this page, the possibility exists that some errors have invaded the machine. Furthermore, there may be certain omissions of physical properties, reaction conditions, necessary equipment, storage and handling requirements, and critical safety data. As with any scientific endeavor, especially chemistry, the necessary safety precautions should be observed at all times.

I do not allow errors to persist on my website once they have been discovered, but I need your help to find them. If you observe an error in any procedure, or a critical omission of essential safety precautions, and you have a valid reference that I can independently verify to back up your claim, please contact me via the error reporting form. If there are omissions in this procedure, such as a missing boiling point, density, etc., please contact me if you can fill in the blanks. I am also interested in receiving any alternate methods, or improvements in the procedure to synthesize this compound. If you are interested in submitting your own information please use the user submission area.

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