2,4-Diaminotoluene

Names
Preferred IUPAC name 4-Methylbenzene-1,3-diamine
Other names 2,4-Toluenediamine
Identifiers
CAS Number	95-80-7 Y
3D model (JSmol)	Interactive image
ChemSpider	6991
ECHA InfoCard	100.002.231
PubChem CID	7261
UNII	IS1AKN4HYB Y
CompTox Dashboard (EPA)	DTXSID4020402
SMILES CC1=C(C=C(C=C1)N)N
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]