2,5-Diaminotoluene: Difference between revisions
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2,5-Diaminotoluene is prepared through electrolytic reduction of 2,5-dinitrotoluene.<ref name=Toxicology>C. Burnett, W. Bergfeld, D. Velsito, C. Klaassen, J. Marks, Jr, R. Shank, T. Slaga, P. Snyder, and F. Andersen "Final Amended Report of the Safety Assessment of Toluene-2,5-Diamine, Toluene-2,5-Diamine Sulfate, and Toluene-3,4-Diamine as Used in Cosmetics" in International Journal of Toxicology, 2010, vol 29, pages 61S-83S</ref> Other methods include the reductive cleavage of 4-amino-2,3'-dimethylazobenzene as well as the condensation of 2-amino-1-methylbenzene and toluene-4-sulphonyl chloride to produce 4-toluenesulphono-2-toluidide which is then coupled with diazotized aminobenzenesulphonic acid and reduced.<ref name=Toxicology/> |
2,5-Diaminotoluene is prepared through electrolytic reduction of 2,5-dinitrotoluene.<ref name=Toxicology>C. Burnett, W. Bergfeld, D. Velsito, C. Klaassen, J. Marks, Jr, R. Shank, T. Slaga, P. Snyder, and F. Andersen "Final Amended Report of the Safety Assessment of Toluene-2,5-Diamine, Toluene-2,5-Diamine Sulfate, and Toluene-3,4-Diamine as Used in Cosmetics" in International Journal of Toxicology, 2010, vol 29, pages 61S-83S</ref> Other methods include the reductive cleavage of 4-amino-2,3'-dimethylazobenzene as well as the condensation of 2-amino-1-methylbenzene and toluene-4-sulphonyl chloride to produce 4-toluenesulphono-2-toluidide which is then coupled with diazotized aminobenzenesulphonic acid and reduced.<ref name=Toxicology/> |
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2,5-Diaminotoluene is a substitute for [[phenylenediamine]] (1,4-diaminobenzene) in commercial hair dyes. It is preferred because of its lower toxicity. However, many home hair dyes |
2,5-Diaminotoluene is a substitute for [[phenylenediamine]] (1,4-diaminobenzene) in commercial hair dyes. It is preferred because of its lower toxicity. However, many home hair dyes still use phenylenediamine. In these applications, these diamines function as a primary intermediate, which means that it is first oxidized with [[hydrogen peroxide]] and then combined with a coupler to form the hair dye.<ref name=Ullmann/> 2,5-Diaminotoluene is commonly used to produce black, drab and warm browns, and shades of blonde and gray hair dyes.<ref name=Toxicology/> |
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2,5-Diaminotoluene is also known to be used in the production of [[dyes]] for textiles, furs, leathers, biological stains and indicators, wood stains, and pigments. Two examples of dyes produced by 2,5-diaminotoluene are Cl Basic Red 2 and Cl Acid Brown 103.<ref name=Toxicology/> |
2,5-Diaminotoluene is also known to be used in the production of [[dyes]] for textiles, furs, leathers, biological stains and indicators, wood stains, and pigments. Two examples of dyes produced by 2,5-diaminotoluene are Cl Basic Red 2 and Cl Acid Brown 103.<ref name=Toxicology/> |
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Revision as of 22:42, 6 October 2011
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| Names | |
|---|---|
| IUPAC name
2,5-diaminotoluene
| |
| Other names
2-methyl-1,4-benzenediamine; toluene-2,5-diamine
| |
| Identifiers | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.221 |
| KEGG | |
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| Properties | |
| C7H10N2 | |
| Molar mass | 122.17 |
| Appearance | off white crystals |
| Density | 1.107 g/cm3 |
| Melting point | 64 °C |
| Boiling point | 273 °C |
| Hazards | |
| Flash point | no |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
2,5-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. 2,5-Diaminotoluene is a colorless crystalline solid that is commonly used in hair coloring.[1]
Formation and use
2,5-Diaminotoluene is prepared through electrolytic reduction of 2,5-dinitrotoluene.[2] Other methods include the reductive cleavage of 4-amino-2,3'-dimethylazobenzene as well as the condensation of 2-amino-1-methylbenzene and toluene-4-sulphonyl chloride to produce 4-toluenesulphono-2-toluidide which is then coupled with diazotized aminobenzenesulphonic acid and reduced.[2]
2,5-Diaminotoluene is a substitute for phenylenediamine (1,4-diaminobenzene) in commercial hair dyes. It is preferred because of its lower toxicity. However, many home hair dyes still use phenylenediamine. In these applications, these diamines function as a primary intermediate, which means that it is first oxidized with hydrogen peroxide and then combined with a coupler to form the hair dye.[1] 2,5-Diaminotoluene is commonly used to produce black, drab and warm browns, and shades of blonde and gray hair dyes.[2]
2,5-Diaminotoluene is also known to be used in the production of dyes for textiles, furs, leathers, biological stains and indicators, wood stains, and pigments. Two examples of dyes produced by 2,5-diaminotoluene are Cl Basic Red 2 and Cl Acid Brown 103.[2]
References
- ^ a b T. Clausen "Hair Preparations" in Ullmann’s Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_571.pub2
- ^ a b c d C. Burnett, W. Bergfeld, D. Velsito, C. Klaassen, J. Marks, Jr, R. Shank, T. Slaga, P. Snyder, and F. Andersen "Final Amended Report of the Safety Assessment of Toluene-2,5-Diamine, Toluene-2,5-Diamine Sulfate, and Toluene-3,4-Diamine as Used in Cosmetics" in International Journal of Toxicology, 2010, vol 29, pages 61S-83S