''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 Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

derivative.

Production and use

It is prepared via methanolysis of 2-chloronitrobenzene: :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 Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin tha ...

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 Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of ...

in the heartwood a reddish brown

azo dye Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N ...

is formed. :

Safety and environmental aspects

''o''-Anisidine is a dangerous pollutant from the production of dyes. It is listed as RCRA

hazardous waste Hazardous waste is waste that has substantial or potential threats to public health or the environment. Hazardous waste is a type of dangerous goods. They usually have one or more of the following hazardous traits: ignitability, reactivity, co ...

, with the code K181. The International Agency for Research on Cancer (IARC) has classified ''o''-anisidine as a Group 2B, possible human carcinogen.

References

External links

* * {{DEFAULTSORT:Anisidine, o- Anilines Hazardous air pollutants IARC Group 2B carcinogens