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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	774521
ChEBI	CHEBI:53619 ;
ChemSpider	6982 ;
ECHA InfoCard	100.002.221
EC Number	202-442-1;
KEGG	C19386 ;
PubChem CID	7252;
UNII	24JO8Z0RJU ;
CompTox Dashboard (EPA)	DTXSID6029123 ;
	InChI InChI=1S/C7H10N2/c1-5-4-6(8)2-3-7(5)9/h2-4H,8-9H2,1H3 Key: OBCSAIDCZQSFQH-UHFFFAOYSA-N ;
	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
REL (Recommended)	Ca
IDLH (Immediate danger)	Ca [N.D.]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 dyes for textiles, furs, leathers, biological stains and indicators, wood stains, and pigments. Two examples of dyes produced by 2,5-diaminotoluene are Cl Basic Red 2 and Cl Acid Brown 103.^[3]

References

^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b T. Clausen (2006). "Hair Preparations". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_571.pub2. ISBN 9783527303854.
^ ^a ^b ^c ^d Burnett, Christina L.; Bergfeld, Wilma F.; Belsito, Donald V.; Klaassen, Curtis D.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Andersen, F. Alan (May 2010). "Final Amended Report of the Safety Assessment of Toluene-2,5-Diamine, Toluene-2,5-Diamine Sulfate, and Toluene-3,4-Diamine as Used in Cosmetics". International Journal of Toxicology. 29 (3_suppl): 61S–83S. doi:10.1177/1091581810361964. ISSN 1091-5818. PMID 20448268. S2CID 35340555.

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-2] T. Clausen (2006). "Hair Preparations". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_571.pub2. ISBN 9783527303854.

[Toxicology-3] Burnett, Christina L.; Bergfeld, Wilma F.; Belsito, Donald V.; Klaassen, Curtis D.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Andersen, F. Alan (May 2010). "Final Amended Report of the Safety Assessment of Toluene-2,5-Diamine, Toluene-2,5-Diamine Sulfate, and Toluene-3,4-Diamine as Used in Cosmetics". International Journal of Toxicology. 29 (3_suppl): 61S–83S. doi:10.1177/1091581810361964. ISSN 1091-5818. PMID 20448268. S2CID 35340555.

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