O-Dianisidine

{{DISPLAYTITLE:''o''-Dianisidine}} {{Chembox | ImageFile = Dianisidine.svg | ImageSize = | ImageAlt = | PIN = 3,3′-Dimethoxy[1,1′-biphenyl]-4,4′-diamine | OtherNames = 3,3'-dimethoxy-4,4’-benzidine |Section1={{Chembox Identifiers | CASNo = 119-90-4 | PubChem = 8411 | EC_number = 204-355-4 | RTECS = DD0875000 | UNNumber = 2811, 2431, 3077 | UNII = MJY508JZXV | ChEBI = 82321 | ChEMBL = 398363 | KEGG = C19231 | ChemSpiderID = 8104 | InChI=1S/C14H16N2O2/c1-17-13-7-9(3-5-11(13)15)10-4-6-12(16)14(8-10)18-2/h3-8H,15-16H2,1-2H3 | InChIKey = JRBJSXQPQWSCCF-UHFFFAOYSA-N | SMILES = COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)OC)N }} |Section2={{Chembox Properties | C=14|H=16|N=2|O=2 | MolarMass = | Appearance = White solid | Density = 1.178 g/cm³ | MeltingPtC = 113 | BoilingPtC = 356 | Solubility = 60 mg/L }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = 206°C | GHSPictograms = {{GHS07}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|302|350}} | PPhrases = {{P-phrases|201|202|264|270|281|301+312|308+313|330|405|501}} | AutoignitionPt = }} }} '''''o''-Dianisidine''' is an organic compound with the formula [(CH₃O)(H₂N)C₆H₃]₂. A colorless or white solid, it is a bifunctional compound derived via the benzidine rearrangement from ''o''-anisidine.

''o''-Dianisidine is a precursor to some azo dyes by formation of the bis(diazonium) derivative, which is coupled to diverse aromatic compounds. Some commercial dyes derived from ''o''-dianisidine include C. I. Direct Blue 1, 15, 22, 84, and 98.<ref name=Ullmann>{{cite encyclopedia|author1=Klaus Hunger|author2=Peter Mischke|author3=Wolfgang Rieper|author4=Roderich Raue|author5=Klaus Kunde|author6=Aloys Engel|title=Azo Dyes|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a03_245|isbn=3527306730 }}.</ref>

''o''-Dianisidine is also used in assaying activity of peroxidase in lab. The general reaction of a peroxidase is as follows. :<chem>ROOR' + \overset{electron\atop donor}{2e^-} + 2H+ ->[\ce{Peroxidase}] {ROH} + R'OH</chem> Where the ROOR' can be hydrogen peroxide, and the electron donor be ''o''-dianisidine.

[[Image:Pontamine sky blue.svg|248 px|thumb|left|Direct Blue 1 is commercial dye, a derivative of o-dianisidine.]]

==Safety== The manufacture and degradation of ''o''-dianisidine, like other benzidene derivatives, has attracted regulatory attention.<ref>{{cite journal|doi=10.1016/j.toxlet.2003.11.016|title=Carcinogenicity of Azo Colorants: Influence of Solubility and Bioavailability|author1=Golka, Klaus |author2=Kopps, Silke |author3=Myslak, Zdislaw W. |journal=Toxicology Letters|year=2004|volume=151|issue=1 |pages= 203–210|pmid=15177655}}</ref> It is also used as a reagent in biochemistry in testing for peroxides.

==References== <references />

{{Chemical agents}}

{{DEFAULTSORT:Dianisidine, o-}} Category:Anilines Category:IARC Group 2B carcinogens Category:Biphenyls Category:Diamines Category:Symmetrical biaryls