Dinitro-ortho-cresol

Dinitro-ortho-cresol
Names
Preferred IUPAC name
2-Methyl-3,5-dinitrophenol
Other names
  • 3,5-Dinitro-ortho-cresol
  • 3,5-Dinitro-o-cresol
  • DNOC
  • 2-Methyl-3,5-dinitrophenol
  • 3,5-Dinitro-2-hydroxytoluene
  • DNC
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C7H6N2O5/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10/h2-3,10H,1H3
  • [O-][N+](=O)c1cc(O)c(c([N+]([O-])=O)c1)C
Properties
C7H6N2O5
Molar mass 198.134 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):
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)
NIOSH (US health exposure limits):
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).

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.

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.

Applications and safety

DNOC is an uncoupler, which means that it interferes with adenosine triphosphate (ATP) production, making it extremely toxic to humans.

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

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

References

  1. 1 2 3 4 5 6 7 8 "#0234". NIOSH Pocket Guide to Chemical Hazards. National Institute for Occupational Safety and Health.
  2. ↑ "Dinitro-o-cresol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 4 December 2014. Retrieved 17 March 2015.
  3. ↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
  4. ↑ Parker, V. H.; Barnes, J. M.; Denz, F. A. (1951). "Some Observations on the Toxic Properties of 3:5-Dinitro-Ortho-Cresol". Occupational and Environmental Medicine. 8 (4): 226. doi:10.1136/oem.8.4.226. PMC 1037342. PMID 14878957.
  5. ↑ Harvey, DG; Bidstrup, PL; Bonnell, JA (1951). "Poisoning by dinitro-ortho-cresol; some observations on the effects of dinitro-ortho-cresol administered by mouth to human volunteers". British Medical Journal. 2 (4722): 13–6. doi:10.1136/bmj.2.4722.13. PMC 2069381. PMID 14839311.
  6. 1 2 "4,6-DINITRO-o-CRESOL (DNOC) (including salts)" (PDF). Environmental Protection Agency. Retrieved 14 December 2023.
  7. ↑ Biegaǹska, Jolanta (1 February 2005). "Neutralization of 4,6-Dinitro- o -cresol Waste Pesticide by Means of Detonative Combustion". Environmental Science & Technology. 39 (4): 1190–1196. doi:10.1021/es035327p.
  8. ↑ "Chemical poisoning -- Dinitrocresol Symptoms, Diagnosis, Treatments and Causes - RightDiagnosis.com". www.rightdiagnosis.com.