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o-Dianisidine

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o-Dianisidine Basic information

Product Name:
o-Dianisidine
Synonyms:
  • o-Dianisidine,3,3′-Dimethoxybenzidine, Fast BlueB
  • 3.3'-Dimethoxybenzidine 1g [119-90-4]
  • 4,4'-Diamino-3,3'-dimethoxybiphenyl 3,3'-Dimethoxybenzidine Fast Blue B
  • 3.3'-DiMethoxy
  • 3,3'-Dimethoxybenzidine Solution, 100ppm
  • [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethoxy-
  • 1’-biphenyl)-4,4’-diamine,3,3’-dimethoxy-(
  • 1’-Biphenyl)-4,4’-diamine,3,3’-dimethoxy-(1
CAS:
119-90-4
MF:
C14H16N2O2
MW:
244.29
EINECS:
204-355-4
Product Categories:
  • Intermediates of Dyes and Pigments
  • Biphenyl & Diphenyl ether
Mol File:
119-90-4.mol
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o-Dianisidine Chemical Properties

Melting point:
137-138 °C(lit.)
Boiling point:
387.21°C (rough estimate)
Density 
1.1079 (rough estimate)
refractive index 
1.6000 (estimate)
Flash point:
403 °F
storage temp. 
Store at RT.
solubility 
H2O: slightly soluble
form 
Crystalline Powder
pka
4.71±0.10(Predicted)
Colour Index 
37235
color 
Pink to beige-brown
Water Solubility 
Soluble in alcohol, benzene, ether, chloroform, acetone, most organic solvents and lipids. Slightly soluble in water.
Merck 
14,2991
BRN 
1879884
CAS DataBase Reference
119-90-4(CAS DataBase Reference)
IARC
2B (Vol. 4, Sup 7) 1987
NIST Chemistry Reference
Benzidine, 3,3'-dimethoxy-(119-90-4)
EPA Substance Registry System
3,3'-Dimethoxybenzidine (119-90-4)
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Safety Information

Hazard Codes 
T
Risk Statements 
45-22
Safety Statements 
53-45
RIDADR 
2811
WGK Germany 
3
RTECS 
DD0875000
TSCA 
Yes
HazardClass 
6.1(a)
PackingGroup 
II
HS Code 
29222990
Hazardous Substances Data
119-90-4(Hazardous Substances Data)

MSDS

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o-Dianisidine Usage And Synthesis

Chemical Properties

o-Dianisidine, crystallizes dimorphically, rarely in needles, with mp 133°C , often in flakes with mp 137-138°C . It forms colorless crystals, but commercial products have a tinge of violet. It is sparingly soluble in water but soluble in alcohol, ether, and benzene. One gram of ethyl acetate dissolves 0.285 g of o-dianisidine at 73°C .

The pure compound is stable upon exposure to air, but commercial products turn violet. o-Dianisidine is resistant to water but sensitive to oxidizing agents.

Uses

o-Dianisidine is a starting material for the production of disazo dyes and pigments.
Like benzidine and o-tolidine, o-dianisidine forms colors with numerous oxidizing agents, e.g., copper, cobalt, and gold ions. o-Dianisidine is quantitatively determined by titration with nitrite using potassium iodide and starch paper as the indicator. o-Dianisidine can be detected in the urine using potassium 1,2-naphthoquinone4-sulfonate after extraction. A rapid and easy method is based on the color formed with cyanogen bromide. Its detection limit is 0.05 mg/kg.
The free o-dianisidine base and the dihydrochloride are marketed in moist forms with a 10-30% water content.

Uses

o-Dianisidine is used almost exclusively as a chemical intermediate for producing dyes and pigments. In 1971, the Society of Dyers and Colourists reported its use in the production of 89 dyes (see Dyes Metabolized to o-Dianisidine, below). o-Dianisidine is also used as a chemical intermediate to produce o-dianisidine diisocyanate for use in adhesives and as a component of polyurethanes. Other uses are as a dye for paper, plastics, rubber, and textiles and as a test substance for detection of metals, thiocyanates, and nitrites (IARC 1974, HSDB 2009).

Preparation

2-Nitroanisole is reduced (H2-catalyst or iron-formic acid) to o-anisidine or (benzidine-type reaction) to o-dianisidine [119-90-4], both of which are important as dye intermediates.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 7077, 1984 DOI: 10.1021/ja00335a035

General Description

Colorless crystals or a light brown powder. Turns violet on standing. Carcinogen.

Air & Water Reactions

Finely powdered material is a significant dust explosion hazard. Insoluble in water.

Reactivity Profile

o-Dianisidine is a weak base. Reacts exothermically with acids. Sensitive to heat, air and prolonged exposure to light.

Fire Hazard

o-Dianisidine is combustible.

Safety Profile

Confirmed carcinogen with experimental tumorigenic data. Moderately toxic by ingestion. Mutation data reported. Combustible when exposed to heat or flame. When heated to decomposition it emits toxic fumes of NOx.

Carcinogenicity

o-Dianisidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

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