Dinitro-ortho-cresol
Chemical compound From Wikipedia, the free encyclopedia
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.
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Names | |
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Preferred IUPAC name
2-Methyl-3,5-dinitrophenol | |
Other names
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Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.007.821 |
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
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) |
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).
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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]
References
External links
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