DNAN

     DNAN, an acronym for 2,4-dinitroanisole, is an insensitive high explosive ether similar to dinitrophenol. Other names for DNAN include 1-methoxy-2,4-dinitro-benzene; 1-methoxy-2,4-dinitrobenzene; 1,3-dinitro-4-methoxybenzene; 2,4-dinitroanisol; 2,4-dinitrophenyl methyl ether; dinitroanisole; DNAns; and NSC 8733. DNAN has been proposed as an ingredient in melt pourable high fragmentation explosives (designated PAX) for use in cannon launched warheads. DNAN has been used as an insect repellant even though it is toxic. The Germans used DNAN in explosive compositions in warheads for the V-1 rocket. It is more stable than TNT, but less powerful. Other isomers of DNAN exist, but only the 2,4 isomer is used as an explosive.

CHEMICALS	APPARATUS
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     Synthesis 1: Prepare fresh potassium methoxide by adding 0.8 g of potassium metal to 5 mL of anhydrous methanol. Prepare a solution of 1 g of 2,2,4,4-tetranitrodiphenyl ether in 10 mL of dimethylformamide in a 25-mL beaker, and then add the potassium methoxide. Keep the reaction mixture at 25 C for 10 minutes and then add to a beaker containing 50-75 mL of water. A precipitate of dinitroanisole will form. Allow several minutes for it to fully precipitate and to settle. Collect this material by filtering and allow it to dry. To the liquid filtrate add enough hydrochloric acid to make the solution slightly acidic to precipitate dinitrophenol, which can be collected by filtration and allowed to dry. Yield of dinitroanisole is 95%, yield of dinitrophenol is 76%. For more information on 2,4-dinitrophenol as well as an additional synthesis please see its section here. Synthesis 2: Prepare a mixture of 205.5 g of 2,4-dinitrochlorobenzene in 160 mL of methyl alcohol. Add 172.7 g of potassium carbonate in small portions over a period of 30 minutes at such a rate that the temperature rises to 60 C. The mixture is then heated under reflux for 2 hours. Allow the mixture to cool to room temperature and add 320 mL of cold water to precipitate the product. Filter to collect the precipitate, wash it thoroughly with water until neutral to litmus paper, and allow it to dry. Final yield of 2,4-dinitroanisole is 195.6 g or nearly 99%. Synthesis 3: Into a 1-L round-bottomed flask prepare a mixture of 175.9 g of ground potassium carbonate, 79.17 g of 2,4-dinitrophenol, 63.6 g of methyl bromide, and 300 mL of methyl isobutyl ketone. The flask is sealed and heated at 115-120 C and 3.45 atm for 3 hours. The flask is then heated at 140-142 C for 5 hours while the pressure rises to 5 atm for a short while eventually dropping to 3 atm by the 5th hour. Allow the mixture to cool to room temperature and distill off the solvent to dryness at 50 C under partial vacuum. Dissolve the residue in a minimum of hot water and filter to collect the insoluble 2,4-dinitroanisole. Wash the collected material with 1% ammonium hydroxide and with water heated to 50 C. Dry the washed crystals at 50 C under vacuum. Final yield of 2,4-dinitroanisole 84.6 g or 91%. Synthesis 4: Into a 500-mL round-bottomed flask prepare a mixture of 4 g of ground potassium carbonate, 18.4 g of 2,4-dinitrophenol, 30 g of methyl iodide, and 150 mL of anhydrous acetone. The mixture is refluxed at atmospheric pressure for 24 hours. Afterwards, allow the solvent to evaporate to dryness under reduced pressure and gentle heating. The residue is extracted several times with small portions of boiling hexane. The extracts are combined and filtered while still hot to remove any undissolved impurities. The filtrate is refrigerated to precipitate crystals of 2,4-dinitroanisole. Filter to collect the crystals and allow them to dry. Final yield is 13 g or 66%. Synthesis 5: Into a 2-L round-bottomed flask prepare a solution of 213 g of melted 2,4-dinitrochlorobenzene dissolved in 632 g of methyl alcohol. While stirring add a solution of 42 g of sodium hydroxide dissolved in 44 mL of water. Add the hydroxide solution at such a rate as to heat the mixture to a gentle reflux. After all of the hydroxide has been added the reaction solution is heated at reflux for 1 hour. Add 800 g of ice to the solution to precipitate crystals of 2,4-dinitroanisole. Filter to collect the precipitate, wash it with 2 L of cold water, and allow it to dry.

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