o-Anisidine

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o-Anisidine
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UN number 2431
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Template:Longitem Template:Chembox Elements/molecular formula
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Appearance Yellow liquid, turns brown upon exposure to air
Density 1.0923 g/cm3
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Solubility soluble in ethanol, diethyl ether, acetone, benzene
Template:Longitem −80.44·10−6 cm3/mol
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Template:Longitem m-Anisidine
p-Anisidine

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o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

Production and use

It is prepared via methanolysis of 2-chloronitrobenzene:[4]

NaOCH3 + ClC6H4NO2 → CH3OC6H4NO2 + NaCl

The resulting o-nitroanisole is reduced to o-anisidine.

o-Anisidine is used in the manufacture of dyes. It is nitrated to give 4-nitroanisidine. It is also a precursor to o-dianisidine.

One special use is as a heartwood indicator. An acid solution of o-anisidine is diazotized by adding a sodium nitrite solution. This mixture is applied to the wood and by reaction with polyphenols in the heartwood a reddish brown azo dye is formed.

File:Direct Blue 15.svg
Direct Blue 15 is an azo dye produced from o-anisidine

Safety and environmental aspects

o-Anisidine is a dangerous pollutant from the production of dyes. It is listed as RCRA hazardous waste, with the code K181.[5] The International Agency for Research on Cancer (IARC) has classified o-anisidine as a Group 2B, possible human carcinogen.[6]

References

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External links

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