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
  • 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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.821 Edit this at Wikidata
  • 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[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):
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).

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.[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

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0234". National Institute for Occupational Safety and Health (NIOSH).
  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. ^ a b "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.