2,4-Diaminotoluene
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Names | |
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Preferred IUPAC name 4-Methylbenzene-1,3-diamine | |
Other names 2,4-Toluenediamine | |
Identifiers | |
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ECHA InfoCard | 100.002.231 ![]() |
PubChem CID |
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Properties | |
Chemical formula | C7H10N2 |
Molar mass | 122.171 g·mol−1 |
Appearance | White solid |
Density | 1.521 g/cm3 |
Melting point | 97 to 99 °C (207 to 210 °F; 370 to 372 K) |
Boiling point | 283 to 285 °C (541 to 545 °F; 556 to 558 K) |
Hazards | |
NIOSH (US health exposure limits): | |
PEL (Permissible) | none[1] |
REL (Recommended) | Ca[1] |
IDLH (Immediate danger) | Ca [N.D.][1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
2,4-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid, although commercial samples are often yellow-tan.[2]
Preparation
It is prepared by hydrogenation of 2,4-dinitrotoluene using a nickel catalyst. Commercial samples often contain up to 20% of the 2,6-isomer.[2]
A laboratory method involves reduction of 2,4-dinitrotoluene with iron powder.[3]
Use
It is mainly used as a precursor to toluene diisocyanate, a precursor to polyurethane. It is as well a degradation product of polyurethane materials produced using toluene diisocyanate.
Its reaction with benzenediazonium chloride gives the cationic azo dye Basic Orange 1. Condensation of 2,4-diaminotoluene with acetaldehyde gives the acridine dye called Basic Yellow 9.[4]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/b/bd/SynthesisBasicYellow9.png/420px-SynthesisBasicYellow9.png)
References
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405
- ^ Mahood, S. A.; Schaffner, P. V. L. (1931). "2,4-Diaminotoluene". Organic Syntheses. 11: 32. doi:10.15227/orgsyn.011.0032.
- ^ Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a27_179