Dinoseb
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Preferred IUPAC name
2-(Butan-2-yl)-4,6-dinitrophenol
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| Other names
2-(sec-Butyl)-4,6-dinitrophenol
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.692 |
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PubChem CID
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| Properties | |
| C10H12N2O5 | |
| Molar mass | 240.21 g/mol |
| Density | 1.35 g/cm3 |
| Melting point | 38-42 °C |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Dinoseb is an herbicide in the dinitrophenol family. The IUPAC name is 2-(butan-2-yl)-4,6-dinitrophenol and its molecular formula is C10H12N2O5. Naturally, dinoseb occurs as orange crystals which cannot dissolve in water easily. Dinoseb is banned as an herbicide in the EU and USA because of its toxicity.
In 1892, dinitro-ortho-cresol (2,4-dinitro-6-methylphenol), a chemical compound closely related to dinoseb, was discovered in Germany and first used as an insecticide. It was later also used as an herbicide and also fungicide characteristics were discovered. In 1945 the ortho-methyl group was replaced by a sec-butyl group, producing dinoseb. This compound had a superior contact and stomach activity on insects and mites. Dinoseb became commercially available in 1945 and was approved for use in the United States based on safety data from Industrial Bio-Test Laboratories. On January 13, 1984 the Danish ship Dana Optima lost 80 drums of Dinoseb during their trip from North Shields (UK) to Esbjerg (DK). After four months 72 drums were found and recovered. Dinoseb was withdrawn from the market in 1986 due to an increased threat of birth defects after female field workers were exposed to the chemical. It could also cause sterility in men who were exposed to the chemical.
Dinoseb is an herbicide that was once widely used for weed-control when producing crops like soybeans, vegetables, fruits and nuts, or citrus. In the present, dinoseb is banned in the EU and USA due to its high toxicity. However, dinoseb is still used in China for example; evidenced by the fact that it is found in rain- and drinking water. Nowadays there are other, safer herbicides that can be used. Dinoseb was also used as an insecticide to protect grapes. On the internet, dinoseb and other dinitrophenols are bought as weight-loss pills. It is very dangerous however, and many people have died of accidental overdose.
The first step in the synthesis of dinoseb is the synthesis of 2-(1-methylpropyl)phenol from 1-butene and phenol. First, 1-butene is protonated so that a secondary carbocation is formed. This can only happen under acidic conditions. The formed carbocation can undergo electrophilic aromatic substitution with phenol. The product of this reaction is 2-(1-methylpropyl)phenol.
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