2,4-Diaminotoluene

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.

2,4-Diaminotoluene
Names
Preferred IUPAC name
4-Methylbenzene-1,3-diamine
Other names
2,4-Toluenediamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.231
UNII
  • CC1=C(C=C(C=C1)N)N
Properties
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

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. NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
  2. Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405
  3. "2,4-DIAMINOTOLUENE". Organic Syntheses. 11: 32. 1931. 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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