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]
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]
^ abcdBurnett, 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.
January 01, 1970
diaminotoluene, organic, compound, with, formula, c6h3, 2ch3, isomer, with, this, formula, colorless, crystalline, solid, although, commercial, samples, often, colored, owing, oxidation, commonly, used, hair, coloring, names, preferred, iupac, name, methylbenz. 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 2 5 Diaminotoluene Names Preferred IUPAC name 2 Methylbenzene 1 4 diamine Other names 2 Methyl 1 4 benzenediamineToluene 2 5 diamine2 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 YKey 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 Y N Infobox referencesFormation and use edit2 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 edit 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 Retrieved from https en wikipedia org w index php title 2 5 Diaminotoluene amp oldid 1198516071, wikipedia, wiki, book, books, library,
