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2,5-Diaminotoluene

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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
3D model (JSmol)
Beilstein Reference 774521
ChEBI
ChemSpider
ECHA InfoCard 100.002.221 Edit this at Wikidata
EC Number
  • 202-442-1
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H10N2/c1-5-4-6(8)2-3-7(5)9/h2-4H,8-9H2,1H3Key: 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/cm
Melting point 64 °C (147 °F; 337 K)
Boiling point 273 °C (523 °F; 546 K)
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Formation and use

2,5-Diaminotoluene is prepared through electrolytic reduction of 2,5-dinitrotoluene. 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.

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. 2,5-Diaminotoluene is commonly used to produce black, drab and warm browns, and shades of blonde and gray hair dyes.

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.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ T. Clausen (2006). "Hair Preparations". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_571.pub2. ISBN 9783527303854.
  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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