90-04-0

Clear, yellowish to reddish or brown liquid with an amine (fishy) odor.

O-ANISIDINE(90-04-0) is sensitive to heat. O-ANISIDINE(90-04-0) is also sensitive to exposure to light. This chemical is incompatible with strong oxidizers. O-ANISIDINE(90-04-0) is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. O-ANISIDINE(90-04-0) will attack some forms of plastics, rubber and coatings. .

This chemical darkens on exposure to air. Insoluble in water.

Strong irritant. Toxic when absorbed through the skin. Possible carcinogen.

Anisidines are used in the manufacture of azo dyes; pharmaceuticals; textile-processing chemicals Incompatibilities: Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Attacks some coatings and some forms of plastic and rubber.

This chemical is combustible.

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

UN2431 Anisidines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

o-Anisidine was produced commercially in the United States from the 1920s until late 1950s. By 2009, worldwide only six industries manufactured o-anisidine, but none produced hydrochloride salt. o-Anisidine was available from 44 suppliers, including 20 US suppliers, and the hydrochloride salt was available from eight suppliers, including five US suppliers. US imports of o-anisidine and its hydrochloride salt are reported in the category ‘o-anisidines, p-anisidines, and p-phenetidine,’ and US exports are reported in the category ‘anisidines, dianisidines, phenetidines, and their salts.’ From 1989 to 2008, imports ranged from a high of over 4.6 million kg in 1996 to zero in 2007 and 2008, and exports ranged from zero to 262 000 kg. Reports filed under the US Environmental Protection Agency’s (EPA) Toxic Substances Control Act Inventory Up Rule indicated that United States production plus imports of o-anisidine totaled 500 000 lb–1 million lb in 1986, 1990, and 2006; 1 million–10 million lb in 1990 and 1998; and 10 000–500 000 lb in 2002.

Anisidine exists as ortho-, meta-, and paraisomers. They have characteristic amine (fishy) odors.
o-Anisidine (or o-methoxyaniline) is an aromatic amine with a methoxyl group ortho to the amino group of aniline. It is a colorless to yellowish, pink, or reddish liquid.o-Anisidine is soluble in water and mineral oils, and miscible with alcohol, benzene, acetone, and diethylether. o-Anisidine hydrochloride, a salt of o-anisidine, is a grayish crystalline solid or powder at room temperature and is soluble in water (NTP, 2011).

Dissolve in combustible solvent (alcohols, benzene, etc.) and spray solution into furnace equipped with afterburner and scrubber, or burn spill residue on sand and soda ash absorbent in a furnace.

Colorless, yellow to reddish liquid with an amine-like odor. Becomes brown on exposure to air.

ChEBI: O-anisidine is a substituted aniline that is aniline in which the hydrogen ortho to the amino group has been replaced by a methoxy group. It is used as a chemical intermediate in the synthesis of azo pigments and dyes. It has a role as a reagent and a genotoxin. It is a monomethoxybenzene, a substituted aniline and a primary amino compound.

Tetrahedron Letters, 24, p. 4733, 1983 DOI: 10.1016/S0040-4039(00)86242-5

o-Anisidine was carcinogenic in experimental animals.

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

Biological. o-Anisidine should be biodegradable according to OECD guidelines (Brown and Labouerer (1983). Chemical/Physical. At influent concentrations (pH 3.0) of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 52, 20, 7.8, and 3.0 mg/g, respectively. At pHs 7 and 9, the GAC adsorption capacities were 110, 50, 23, and 10 mg/g at influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, respectively (Dobbs and Cohen, 1980).

It is separated from the m-and p-isomers by steam distillation. It is also separated from its usual synthetic precursor o-nitroanisole by dissolving it in dilute HCl (pH <2.0) extracting the nitro impurity with Et2O, adjusting the pH to ~8.0 with NaOH, extracting the amine into Et2O or steam distilling. Extract the distillate with Et2O, dry the extract (Na2SO4), filter, evaporate and fractionate the residual oil. Protect the almost colourless oil from light which turns it yellow in color. [Biggs & Robinson J Chem Soc 3881961, Nodzu et al. Yakugaku Zasshi (J Pharm Soc Japan) 71 713, 715 1951, Beilstein 13 IV 806.]

It is primarily metabolized by cytochrome P450 isozymes, and it forms two o-anisidine–DNA adducts with DNA. It causes DNA damage by a metabolite in the presence of metals such as Cu(II). It can also cause Cu(II)-mediated oxidative DNA damage.