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2,4-Dinitrophenol

2,4-Dinitrophenol
2,4-Dinitrophenol.svg
2,4-Dinitrophenol 3D.png
2,4-Dinitrophenol.jpg
Sample of pure compound
Names
Preferred IUPAC name
2,4-Dinitrophenol
Other names
Solfo Black
Identifiers
51-28-5 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:42017 YesY
ChEMBL ChEMBL273386 YesY
ChemSpider 1448 YesY
DrugBank DB04528 YesY
ECHA InfoCard 100.000.080
KEGG C02496 YesY
PubChem 1493
UNII Q13SKS21MN YesY
UN number 0076, 1320
Properties
C6H4N2O5
Molar mass 184.11 g·mol−1
Density 1.683 g/cm3
Melting point 108 °C (226 °F; 381 K)
Boiling point 113 °C (235 °F; 386 K)
Acidity (pKa) 4.114
-73.1·10−6 cm3/mol
Hazards
R-phrases R10 R23 R24 R25 R33
S-phrases (S1) (S2) S28 S37 S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g., fluorine Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC6H3(NO2)2. It is a yellow, crystalline solid that has a sweet, musty odor. It sublimes, is volatile with steam, and is soluble in most organic solvents as well as aqueous alkaline solutions. It is a precursor to other chemicals and is biochemically active, inhibiting energy (adenosine triphosphate, ATP) production in cells with mitochondria. Its use in high doses as a dieting aid has been identified with severe side-effects, including a number of deaths.

DNP is produced by hydrolysis of 1-chloro-2,4-dinitrobenzene.

Commercial DNP is used as an antiseptic and as a pesticide. It is a chemical intermediate in the production of sulfur dyes, wood preservatives, and some herbicides including dinoseb and dinoterb. DNP has also been used to make photographic developers and explosives.

In living cells, DNP acts as a proton ionophore, an agent that can shuttle protons (hydrogen cations) across biological membranes. It dissipates the proton gradient across and chloroplast membranes, collapsing the proton motive force that the cell uses to produce most of its ATP chemical energy. Instead of producing ATP, the energy of the proton gradient is lost as heat.

DNP is often used in biochemistry research to help explore the bioenergetics of chemiosmotic and other membrane transport processes.

DNP is considered to have high acute toxicity. Acute oral exposure to DNP has resulted in increased basal metabolic rate, nausea, vomiting, sweating, dizziness, headache, and loss of weight. Chronic oral exposure to DNP can lead to the formation of cataracts and skin lesions and has caused effects on the bone marrow, central nervous system, and cardiovascular system.


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