Last updated
2,5-Diaminotoluol Structural Formula V1.svg
Preferred IUPAC name
Other names
3D model (JSmol)
ECHA InfoCard 100.002.221 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-442-1
PubChem CID
  • InChI=1S/C7H10N2/c1-5-4-6(8)2-3-7(5)9/h2-4H,8-9H2,1H3 Yes check.svgY
  • CC1=C(C=CC(=C1)N)N
Molar mass 122.17
Appearanceoff white crystals
Density 1.107 g/cm3
Melting point 64 °C (147 °F; 337 K)
Boiling point 273 °C (523 °F; 546 K)
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
H301, H312, H317, H319, H332, H411
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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<i>p</i>-Phenylenediamine Chemical compound

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<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

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<i>o</i>-Phenylenediamine Chemical compound

o-Phenylenediamine (OPD) is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. OPD is a white compound although samples appear darker owing to oxidation by air. It is isomeric with m-phenylenediamine and p-phenylenediamine.

<i>m</i>-Phenylenediamine Chemical compound

m-Phenylenediamine, also called 1,3-diaminobenzene, is an organic compound with the formula C6H4(NH2)2. It is an isomer of o-phenylenediamine and p-phenylenediamine. This aromatic diamine is a colourless solid that appears as needles, but turns red or purple on exposure to air due to formation of oxidation products. Samples often come as colourless flakes and may darken in storage.

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Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phenazine crystallizes in yellow needles, which are only sparingly soluble in alcohol. Sulfuric acid dissolves it, forming a deep-red solution.

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<i>o</i>-Anisidine Chemical compound

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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.

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  1. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0620". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 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. 1 2 3 4 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.