Dinitro-ortho-cresol

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Dinitro-ortho-cresol
2-Methyl-3,5-dinitrophenol.svg
Identifiers
CAS number 497-56-3 YesY
PubChem 68131
ChemSpider 61439
Jmol-3D images Image 1
Properties
Molecular formula C7H6N2O5
Molar mass 198.13 g mol−1
Density 1.58 g/cm3
Melting point 86.5 °C
Boiling point 312 °C
Except where noted otherwise, 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.

Preparation[edit]

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.[1]

Applications and safety[edit]

This toxicant interferes with adenosine triphosphate (ATP) production.[2][3]

Symptoms of dinitro-ortho-cresol poisoning, due to ingestion or other forms of exposure, include confusion, headache, shortness of breath, and sweating.[4]

References[edit]

  1. ^ Gerald Booth "Nitro Compounds, Aromatic" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a17 411
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Chemical poisoning - Dinitrocresol

External links[edit]