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by | Mar 5, 2018 | Nut Trees

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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]

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

References

  1. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ 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
  3. ^ Mahood, S. A.; Schaffner, P. V. L. (1931). "2,4-Diaminotoluene". Organic Syntheses. 11: 32. doi:10.15227/orgsyn.011.0032.
  4. ^ 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
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