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

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
  • 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).
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

This toxicant is an uncoupler, which means that it interferes with adenosine triphosphate (ATP) production.[4][5]

Symptoms of dinitro-ortho-cresol poisoning, due to ingestion or other forms of exposure, include confusion, headache, shortness of breath, and sweating.[6]

References
  1. 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. "Chemical poisoning -- Dinitrocresol Symptoms, Diagnosis, Treatments and Causes - RightDiagnosis.com". www.rightdiagnosis.com.
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