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2127733

2,4-Dinitrophenol

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2127733

2,4-Dinitrophenol

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2,4-Dinitrophenol

2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC6H3(NO2)2. It has been used in explosives manufacturing and as a pesticide and herbicide.

In humans, DNP causes dose-dependent mitochondrial uncoupling, causing the rapid loss of ATP as heat and leading to uncontrolled hyperthermia—up to 44 °C (111 °F)—and death in case of overdose. Researchers noticed its effect on raising the basal metabolic rate in accidental exposure and developed it as one of the first weight loss drugs in the early twentieth century. DNP was banned from human use by the end of the 1930s due to its risk of death and toxic side effects. DNP continues to be used after its ban and experienced a resurgence in popularity after it became available on the Internet.

DNP has the chemical formula HOC6H3(NO2)2. As a solid, it is a yellow, crystalline and has a sweet, musty odor. It sublimates, is volatile with steam, and is soluble in most organic solvents as well as aqueous alkaline solutions. DNP is a member of the dinitrophenols chemical family.

DNP can be produced by hydrolysis of 2,4-dinitrochlorobenzene. Other routes of DNP synthesis include nitration of monochlorobenzene, nitration of benzene with nitrogen dioxide and mercurous nitrate, oxidation of 1,3-dinitrobenzene, and nitration of phenol with nitric acid.

A dust explosion is possible with DNP in powder or granular form in the presence of air. DNP may explosively decompose when submitted to shock, friction or concussion, and may explode upon heating. DNP forms explosive salts with strong bases as well as ammonia, and emits toxic fumes of nitrogen dioxide when heated to decomposition. DNP's explosive strength is 81% that of TNT, based on the Trauzl lead block test.

Historically, DNP has been used as an antiseptic and as a non-selective bioaccumulating pesticide.

DNP was particularly useful as a herbicide alongside other closely related dinitrophenol herbicides like 2,4-dinitro-o-cresol (DNOC), dinoseb and dinoterb. Since 1998 DNP has been withdrawn from agricultural use. Currently, there are no actively registered pesticides containing DNP in the United States or Europe. Dinoseb is used industrially as a polymerisation inhibitor during styrene production. In 2023, the Home Office said it could not determine any legitimate industrial uses for DNP in the United Kingdom.

It is a chemical intermediate in the production of sulfur dyes, wood preservatives and picric acid. A precursor to 2,4,6-trinitrotoluene (TNT), DNP has also been used to make photographic developers and explosives. DNP is classified as an explosive in the United Kingdom and the United States.

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