o-Dianisidine

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
Dianisidine.svg
Names
IUPAC name
4-(4-amino-3-methoxyphenyl)-2-methoxyaniline
Other names
2,2'-dimethoxy-4,4’-benzidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.960 Edit this at Wikidata
EC Number
  • 204-355-4
KEGG
RTECS number
  • DD0875000
UNII
UN number 2811, 2431, 3077
  • 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
    Key: JRBJSXQPQWSCCF-UHFFFAOYSA-N
  • COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)OC)N
Properties
C14H16N2O2
Molar mass 244.294 g·mol−1
Appearance White solid
Density 1.178 g/cm3
Melting point 113 °C (235 °F; 386 K)
Boiling point 356 °C (673 °F; 629 K)
60 mg/l
Hazards
GHS pictograms GHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H302, H350
P201, P202, P264, P270, P281, P301+312, P308+313, P330, P405, P501
Flash point 206°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[1]

o-Dianisidine is also used in assaying activity of peroxidase in lab. The general reaction of a peroxidase is as follows.

Where the ROOR' can be hydrogen peroxide, and the electron doner be o-dianisidine.

Direct Blue 1 is commercial dye, a derivative of o-dianisidine.

SafetyEdit

The manufacture and degradation of o-dianisidine, like other benzidene derivatives, has attracted regulatory attention.[2] It is also used as a reagent in biochemistry in testing for peroxides.

ReferencesEdit

  1. ^ Klaus Hunger; Peter Mischke; Wolfgang Rieper; Roderich Raue; Klaus Kunde; Aloys Engel (2005). "Azo Dyes". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245..
  2. ^ Golka, Klaus; Kopps, Silke; Myslak, Zdislaw W. (2004). "Carcinogenicity of Azo Colorants: Influence of Solubility and Bioavailability". Toxicology Letters. 151: 203–210. doi:10.1016/j.toxlet.2003.11.016. PMID 15177655.CS1 maint: uses authors parameter (link)