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o-Dianisidine

From Wikipedia, the free encyclopedia
O-Dianisidine
Names
Preferred IUPAC name
3,3′-Dimethoxy[1,1′-biphenyl]-4,4′-diamine
Other names
3,3'-dimethoxy-4,4’-benzidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.003.960Edit this at Wikidata
EC Number
  • 204-355-4
KEGG
RTECS number
  • DD0875000
UNII
UN number2811, 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 mass244.294 g·mol−1
AppearanceWhite solid
Density1.178 g/cm3
Melting point113 °C (235 °F; 386 K)
Boiling point356 °C (673 °F; 629 K)
60 mg/L
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Danger
H302,H350
P201,P202,P264,P270,P281,P301+P312,P308+P313,P330,P405,P501
Flash point206°C
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

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 thebenzidine rearrangement fromo-anisidine.

o-Dianisidine is a precursor to someazo dyes by formation of the bis(diazonium) derivative, which is coupled to diverse aromatic compounds. Some commercial dyes derived fromo-dianisidine include C. I.Direct Blue 1,15,22,84, and98.[1]

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

ROOR+2eelectrondonor+2H+PeroxidaseROH+ROH{\displaystyle {\ce {ROOR'+{\overset {electron \atop donor}{2e^{-}}}+2H+->[{\ce {Peroxidase}}]{ROH}+R'OH}}}

Where the ROOR' can behydrogen peroxide, and the electron donor beo-dianisidine.

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

Safety

[edit]

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

References

[edit]
  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.ISBN 3527306730..
  2. ^Golka, Klaus; Kopps, Silke; Myslak, Zdislaw W. (2004). "Carcinogenicity of Azo Colorants: Influence of Solubility and Bioavailability".Toxicology Letters.151 (1):203–210.doi:10.1016/j.toxlet.2003.11.016.PMID 15177655.
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