2,5-Diaminotoluene

2,5-Diaminotoluene

Names
Preferred IUPAC name 2-Methylbenzene-1,4-diamine
Other names 2-Methyl-1,4-benzenediamine Toluene-2,5-diamine 2,5-Diaminotoluene
Identifiers
CAS Number	95-70-5 Y
3D model ( JSmol )	Interactive image
Beilstein Reference	774521
ChEBI	CHEBI:53619 Y
ChemSpider	6982 Y
ECHA InfoCard	100.002.221
EC Number	202-442-1
KEGG	C19386 N
PubChem CID	7252
UNII	24JO8Z0RJU Y
CompTox Dashboard (EPA)	DTXSID6029123
InChI InChI=1S/C7H10N2/c1-5-4-6(8)2-3-7(5)9/h2-4H,8-9H2,1H3 Y Key: OBCSAIDCZQSFQH-UHFFFAOYSA-N Y
SMILES CC1=C(C=CC(=C1)N)N
Properties
Chemical formula	C7H10N2
Molar mass	122.17
Appearance	off white crystals
Density	1.107 g/cm3
Melting point	64 °C (147 °F; 337 K)
Boiling point	273 °C (523 °F; 546 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H317, H319, H332, H411
Precautionary statements	P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, P501
Flash point	no
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). N verify (what is YN ?) Infobox references

2,5-Diaminotoluene is an organic compound with the formula C₆H₃(NH₂)₂CH₃. It is one isomer of six with this formula. 2,5-Diaminotoluene is a colorless crystalline solid, although commercial samples are often colored owing to air oxidation. It is commonly used in hair coloring.^[2]

Formation and use

2,5-Diaminotoluene is prepared through electrolytic reduction of 2,5-dinitrotoluene.^[3] Other methods include the reductive cleavage of 4-amino-2,3'-dimethylazobenzene as well as the condensation of 2-amino-1-methylbenzene and toluene-4-sulphonyl chloride to produce 4-toluenesulphono-2-toluidide which is then coupled with diazotized aminobenzenesulphonic acid and reduced.^[3]

2,5-Diaminotoluene is a substitute for phenylenediamine (1,4-diaminobenzene) in commercial hair dyes. It is preferred because of its lower toxicity. However, many home hair dyes still use phenylenediamine. In these applications, these diamines function as a primary intermediate, which means that it is first oxidized with hydrogen peroxide and then combined with a coupler to form the hair dye.^[2] 2,5-Diaminotoluene is commonly used to produce black, drab and warm browns, and shades of blonde and gray hair dyes.^[3]

2,5-Diaminotoluene is also known to be used in the production of