Dinitro-ortho-cresol

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH₃C₆H₂(NO₂)₂OH. It is a yellow solid that is only slightly soluble in water. It is extremely toxic to humans and was previously used as a herbicide and insecticide.

Dinitro-ortho-cresol

Names
Preferred IUPAC name 2-Methyl-3,5-dinitrophenol
Other names 3,5-Dinitro-ortho-cresol 3,5-Dinitro-o-cresol 4,6-Dinitro-2-hydroxytoluene DNOC 2-Methyl-3,5-dinitrophenol 4,6-Dinitro-o-cresol 3,5-Dinitro-2-hydroxytoluene 4,6-Dinitro-2-methyl phenol DNC
Identifiers
CAS Number	497-56-3 Y
3D model (JSmol)	Interactive image
ChemSpider	61439
ECHA InfoCard	100.007.821
PubChem CID	68131
CompTox Dashboard (EPA)	DTXSID1022053
InChI InChI=1S/C7H6N2O5/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10/h2-3,10H,1H3
SMILES [O-][N+](=O)c1cc(O)c(c([N+]([O-])=O)c1)C
Properties
Chemical formula	C7H6N2O5
Molar mass	198.134 g·mol−1
Appearance	Yellow solid[1]
Odor	Odorless[1]
Density	1.58 g/cm3
Melting point	86.5 °C (187.7 °F; 359.6 K)
Boiling point	312 °C (594 °F; 585 K)
Solubility in water	0.01% (20°C)[1]
Vapor pressure	0.00005 mmHg (20°C)[1]
Hazards
Flash point	noncombustible[1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	7 mg/kg (oral, rat) 50 mg/kg (oral, cat) 21 mg/kg (oral, mouse) 24.6 mg/kg (oral, rabbit) 24.6 mg/kg (oral, guinea pig) 31 mg/kg (oral, rat)[2]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.2 mg/m3 [skin][1]
REL (Recommended)	TWA 0.2 mg/m3 [skin][1]
IDLH (Immediate danger)	5 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation

This compound is prepared by disulfonation of o-cresol. The resulting disulfonate is then treated with nitric acid to give DNOC. A variety of related derivatives are known including those where the methyl group is replaced by sec-butyl (dinoseb), tert-butyl (dinoterb), and 1-methylheptyl (dinocap). These are prepared by the direct nitration of the alkyphenols.^[3]

Applications and safety

DNOC is an uncoupler, which means that it interferes with adenosine triphosphate (ATP) production,^[4][5] making it extremely toxic to humans.^[6]

DNOC was one of the earliest pesticides developed, being used as an insecticide since the 1890s and a herbicide since the 1930s.^[7] It was banned for use as a pesticide in the United States in 1991.^[6]

Symptoms of dinitro-ortho-cresol poisoning, due to ingestion or other forms of exposure, include confusion, fever, headache, shortness of breath, and sweating.^[8]