2,4-Dinitrophenol

2,4-Dinitrophenol
	Chemical structure
	Compound sample
Identifiers
CAS Number	51-28-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42017 ;
ChEMBL	ChEMBL273386 ;
ChemSpider	1448 ;
DrugBank	DB04528 ;
ECHA InfoCard	100.000.080
KEGG	C02496 ;
PubChem CID	1493;
UNII	Q13SKS21MN ;
CompTox Dashboard (EPA)	DTXSID0020523 ;
	InChI InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H Key: UFBJCMHMOXMLKC-UHFFFAOYSA-N ;
	SMILES O=[N+]([O-])c1cc(ccc1O)[N+]([O-])=O;
Properties
Chemical formula	HOC6H3(NO2)2
Molar mass	184.107 g·mol−1
Appearance	Yellow orthorhombic crystals (from water) or platelets (from alcohol)
Odor	Sweet, musty
Density	1.683 g/cm3 (24 °C (75 °F; 297 K)); 1.483 g/cm3 (72.5 °C (162.5 °F; 345.6 K));
Melting point	112–114 °C (234–237 °F; 385–387 K)
Boiling point	decomposes (sublimes when carefully heated)
Solubility in water	5.6 g/L (18 °C (64 °F; 291 K))
Solubility in Ethyl acetate	15.5 g/100g (15 °C (59 °F; 288 K)); 39.5 g/100g (50 °C (122 °F; 323 K));
Solubility in Acetone	35.9 g/100g (15 °C); 98.3 g/100g (50 °C);
Solubility in Ethanol	3.8 g/100g (15 °C); 13.3 g/100g (50 °C);
Solubility in Methanol	5.0 g/100g (15 °C); 16.9 g/100g (50 °C);
Solubility in Pyridine	21.0 g/100g (15 °C); 71.0 g/100g (50 °C);
Solubility in Toluene	6.4 g/100g (15 °C); 20.0 g/100g (50 °C);
log P	1.54
Vapor pressure	1.99 hPa (0.0289 psi) (18 °C (64 °F; 291 K))
Acidity (pKa)	4.09
Explosive data
Shock sensitivity	2kg, 17" (Picatinny Arsenal apparatus)
Detonation velocity	5,000 m/s (16,000 ft/s)
RE factor	81% TNT (Trauzl test)
Pharmacology
Drug class	Uncoupling agents
Routes of; administration	Oral
	Pharmacokinetics:
Metabolism	Nitro reduction
Biological half-life	Unknown
Legal status	AU: S10 (Dangerous substance); BR: Class F4 (Other prohibited substances); UK: Regulated poison; US: Investigational new drug, Orphan drug (Huntington's disease); Banned for human consumption in many countries.;
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H228, H300, H311+H331, H372, H400
Precautionary statements	P210, P240, P241, P260, P264, P270, P271, P273, P280, P301+P310+P330, P302+P352+P312, P304+P340+P311, P314, P362, P370+P378, P391, P403+P233, P405, P501
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	71 mg/kg (rat, oral); 72 mg/kg (mouse, oral);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,4-Dinitrophenol (2,4-DNP or simply DNP) is an organic compound with the formula HOC₆H₃(NO₂)₂. It occurs as yellow crystals or platelets. 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.