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Dinitro-ortho-cresol
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| Names |
| IUPAC name
2-Methyl-3,5-dinitrophenol
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| 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
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| Identifiers |
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CAS Number
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497-56-3 Y |
| 3D model (Jmol) |
Interactive image |
| ChemSpider |
61439 |
| ECHA InfoCard |
100.007.821 |
| PubChem |
68131 |
InChI
-
InChI=1S/C7H6N2O5/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10/h2-3,10H,1H3
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SMILES
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[O-][N+](=O)c1cc(O)c(c([N+]([O-])=O)c1)C
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| Properties |
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Chemical formula
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C7H6N2O5 |
| Molar mass |
198.13 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) |
|
Solubility in water
|
0.01% (20°C)[1] |
| Vapor pressure |
0.00005 mmHg (20°C)[1] |
| Hazards |
| Flash point |
noncombustible [1] |
| 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)[2] |
| US health exposure limits (NIOSH): |
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PEL (Permissible)
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TWA 0.2 mg/m3 [skin][1] |
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REL (Recommended)
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TWA 0.2 mg/m3 [skin][1] |
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IDLH (Immediate danger)
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5 mg/m3[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references |
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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.
Contents
- 1 Preparation
- 2 Applications and safety
- 3 References
- 4 External links
Preparation
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.[3]
Applications and safety
This toxicant 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
- ^ a b c d e f g h "NIOSH Pocket Guide to Chemical Hazards #0234". National Institute for Occupational Safety and Health (NIOSH).
- ^ "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.
- ^ Gerald Booth "Nitro Compounds, Aromatic" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_411
- ^ 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.
- ^ 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.
- ^ Chemical poisoning - Dinitrocresol
External links
- World Health Organization
- CDC - NIOSH Pocket Guide to Chemical Hazards
English Journal
- Study of mass transfer in a dynamic hollow-fibre liquid phase microextraction system.
- Hansson H, Colmsjö A, Nilsson U.SourceDepartment of Analytical Chemistry, Stockholm University, Stockholm, Sweden.
- Journal of separation science.J Sep Sci.2010 Jan;33(1):112-9.
- The extraction characteristics of a dynamic hollow-fibre liquid phase microextraction system were investigated by studying the mass transfer and diffusion rates of dinitrophenols from plasma samples over the liquid membrane (dihexylether). The measured diffusion coefficients were compared with theor
- PMID 20024928
- Adsorption effect on the degradation of 4,6-o-dinitrocresol and p-nitrophenol in a montmorillonite clay slurry by AFT.
- Ye P, Lemley AT.SourceGraduate Field of Environmental Toxicology, Cornell University, 209 MVR Hall, Ithaca, NY 14853, USA.
- Water research.Water Res.2009 Mar;43(5):1303-12. Epub 2009 Jan 8.
- The adsorption and degradation of 4,6-o-dinitrocresol (DNOC) and p-nitrophenol (PNP) in SWy-2 montmorillonite clay slurry were investigated. The pH and type of cation of the slurry were varied. Results showed that adsorption of DNOC and PNP increased at lower pH values, and when pH < pKa(4.4) of
- PMID 19167019
Japanese Journal
Related Links
- dinitrocresol see dinitro-orthocresol. ... Use of Prostab eliminates the need for dinitrophenol and dinitrocresol products, which are said to be somewhat effective in controlling tar but require stringent regulatory reporting in the U.
- Dinitrocresol all about dinitrocresol helpful information about dinitrocresol ... As soon as possible we will add more links Dinitrocresol If you want to quickly find the pages about a particular topic as dinitrocresol use the following ...
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