2,4-Diaminotoluene

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2,4-Diaminotoluene
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Names
IUPAC name
4-Methylbenzene-1,3-diamine
Other names
2,4-Toluenediamine
Identifiers
95-80-7
ChemSpider 6991
Jmol 3D model Interactive image
PubChem 7261
  • CC1=C(C=C(C=C1)N)N
Properties
C7H10N2
Molar mass 122.17 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)
Vapor pressure {{{value}}}
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. 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.[1]

It is mainly used as a precursor to toluene diisocyanate, a precursor to polyurethane.

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.[2]

Synthesis of C.I. Basic Yellow 9, an acridine dye.

References

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  1. Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405
  2. 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