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Dinitrocresol

Dinitro-ortho-cresol
2-Methyl-3,5-dinitrophenol.svg
Names
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
497-56-3 YesY
3D model (Jmol) Interactive image
ChemSpider 61439
ECHA InfoCard 100.007.821
PubChem 68131
Properties
C7H6N2O5
Molar mass 198.13 g·mol−1
Appearance yellow solid
Odor odorless
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)
Vapor pressure 0.00005 mmHg (20°C)
Hazards
Flash point noncombustible
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)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 0.2 mg/m3 [skin]
REL (Recommended)
TWA 0.2 mg/m3 [skin]
IDLH (Immediate danger)
5 mg/m3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. DNOC and some related derivatives have been used as herbicides.

This compound is prepared by dinitration 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.

This toxicant interferes with adenosine triphosphate (ATP) production.

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


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