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Synthesis of dinitrophenol

Dinitrophenol is a very versatile chemical that has been used as an explosive, a pesticide, and as a pharmaceutical compound.  The explosive properties of dinitrophenol are similar to TNT, with a lower detonation velocity and greater stability, but dinitrophenol is rarely used alone.  Rather it is used in admixture with other high explosives, mostly for shells.

During WWI workers who physically handled dinitrophenol while manufacturing artillery shells were observed to experience significant weight loss over the course of their employment.  It turns out that dinitrophenol in small quantities is an extremely effective weight loss drug, and this discovery led to it being one of the first prescription weight loss compounds.  In fact dinitrophenol is still one of the single most effective weight loss compounds in existence.

Dinitrophenol works by stimulating the metabolism.  Modern weight loss drugs that stimulate the metabolism only improve metabolic rates by 2-3%, but dinitrophenol can boost the metabolism by as much as 10000% or more.  Dinitrophenol works by uncoupling of electron transport from ATP synthesis allows rapid oxidation of Krebs substrates.  What this boils down to is dinitrophenol consumes a cells fuel and burns it directly to heat.  Without this fuel the cells are forced to use fat to supply their energy.  Unfortunately, the very effectiveness of dinitrophenol in producing heat from a cells energy is what makes it so dangerous, and deadly.  The heat generated by dinitrophenol will cook you alive in hours, or cause brain damage.

Dinitrophenol is now banned by the FDA because it is far too dangerous to be used by ordinary people.  Ordinary people are stupid, and stupid people think if they can lose a little weight by taking one pill, they can lose a lot of weight by taking two or more pills.  That might work with aspirin, but the difference between a therapeutic dose and a lethal dose of dinitrophenol is very narrow.  Hundreds of people have overdosed on dinitrophenol by misusing the drug.  Even so, dinitrophenol is still a very effective weight loss supplement if you are responsible enough use it wisely.

The same properties that make dinitrophenol a dangerous drug also make it an effective pesticide. 

Dinitrophenol is a very stable high explosive with properties similar to TNT.  There are several isomers of dinitrophenol, but the most useful and easiest to prepare is 2,4-dinitrophenol.  Dinitrophenol is rarely used alone as an explosive, but rather it is used in admixture with other high explosives, mostly for shells.  While more stable than TNT, dinitrophenol has a lower detonation velocity.  Dinitrophenol forms many useful explosive salts with certain metal compounds some of which are described herein.

Dinitrophenol is also an extremely deadly compound.  It can be inhaled or absorbed through the skin.  It raises the body temperature and will kill you.  This interesting side effect is due to a massive increase in metabolism that forces the body to burn fat.  For this reason it was the first prescribed drug for obesity starting in the 1930’s, but was banned shortly thereafter.  It made a resurgence in the 1990’s among body builders, and is still used today.  The problem is because it raises metabolism so much your body produces an excessive amount of heat, and this is what kills you.  Take too much and you will fry your organs.  However, one can lose over 2 pounds of fat a day or more if you are careful and drink lots of water.

Dinitrophenol is also a pesticide and a fungicide sold under the trade name Chemox PE.  It is most often used to control citrus red mites.  Various dinitrophenol derivatives have been made, but are all banned due to mutagenic properties on fetuses.


CxHyOz
b.p. ? °C mass ? g/mol
m.p. ? °C CAS# 51-28-5
den. ? g/mL v.det. ? m/s

Aldifen
1,3-dinitro-4-hydroxybenzene
2,4-dinitrophenol
a-dinitrophenol
Dinofan
2,4-DNP
DNP
Fenoxyl Carbon N
1-hydroxy-2,4-dinitrobenzene
Nitrophen
Nitrophene
NSC 1532
phenol, 2,4-dinitro-
phenol, a-dinitro-


dinitrophenol

dinitrophenol

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-dinitroaniline as well as an additional synthesis please see its section here.

Synthesis 2:
Prepare a solution of 1 g of 2,2,4,4-tetranitrodiphenyl ether in 10 mL of dimethylformamide in a test tube and bubble gaseous ammonia through the solution for 15 minutes while maintaining a temperature of 25 C.  The reaction is then poured into a beaker containing 50-75 mL of water.  A precipitate of dinitroaniline 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 dinitroaniline is 85%, yield of dinitrophenol is 65%.

An alternative to this process is to use only 0.5 g of 2,2,4,4-tetranitrodiphenyl ether in dimethylformamide and to use 0.28 g of 25% aqueous ammonia instead of gaseous ammonia.  The mixture is sealed in a pressure reaction vessel and heated to 100 C for 15 minutes at a pressure of 4 to 5 atm.  Yield of dinitroaniline is 90%, yield of dinitrophenol is 65%.

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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