90-04-0 Usage
Description
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.
Chemical Properties
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).
Physical properties
Colorless, yellow to reddish liquid with an amine-like odor. Becomes brown on exposure to air.
Uses
Different sources of media describe the Uses of 90-04-0 differently. You can refer to the following data:
1. Similar to other aromatic amines, o-anisidine may cause methemglobinemia and cancer in humans. It is used mainly as an intermediate for the production of azo dyes and pigments. Other industrial uses of o-anisidine include synthesis of other dyes and pharmaceuticals, as a corrosion inhibitor for steel, and as an antioxidant for polymercaptan resins (IARC, 1999; HSDB, 2012).
Intermediate for azo dyes and for guaiacol.
2. In the preparation of azo dyes; corrosion
inhibitor; chemical intermediate
3. It is primarily used as a chemical intermediate in the production
of pigments, dyes, pharmaceuticals, and fragrances.
o-Anisidine hydrochloride is used as a chemical intermediate in
the production of numerous azo and triphenylmethane dyes
and pigments (e.g., C.I. direct red 72, disperse orange 29, direct
yellow 44, direct red 24, and acid red 4); in the production of
pharmaceuticals, including the expectorant guaiacol; as
a corrosion inhibitor for steel; and as an antioxidant for polymercaptan
resins.
Synthesis Reference(s)
Tetrahedron Letters, 24, p. 4733, 1983 DOI: 10.1016/S0040-4039(00)86242-5
General Description
Clear, yellowish to reddish or brown liquid with an amine (fishy) odor.
Air & Water Reactions
o-Anisidine darkens on exposure to air. Insoluble in water.
Reactivity Profile
o-Anisidine is sensitive to heat. o-Anisidine is also sensitive to exposure to light. o-Anisidine is incompatible with strong oxidizers. o-Anisidine is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. o-Anisidine will attack some forms of plastics, rubber and coatings. .
Hazard
Strong irritant. Toxic when absorbed
through the skin. Possible carcinogen.
Health Hazard
o-Anisidine was carcinogenic in
experimental animals.
Fire Hazard
o-Anisidine is combustible.
Safety Profile
Confirmed carcinogen.
Moderately toxic by ingestion. Mutation data
reported. When heated to decomposition it
emits toxic fumes of NOx.
Environmental fate
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).
Purification Methods
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.]
Toxicity evaluation
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.
Check Digit Verification of cas no
The CAS Registry Mumber 90-04-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 90-04:
(4*9)+(3*0)+(2*0)+(1*4)=40
40 % 10 = 0
So 90-04-0 is a valid CAS Registry Number.
90-04-0Relevant articles and documents
Rat liver microsomal metabolism of o-aminophenol and N-(2-methoxyphenyl) hydroxylamine, two metabolites of the environmental pollutant and carcinogen o-anisidine in humans
Naiman, Karel,Hodek, Petr,Liberda, Jiri,Schmeiser, Heinz H.,Frei, Eva,Stiborova, Marie
, p. 1229 - 1247 (2010)
o-Aminophenol and N-(2-methoxyphenyl)hydroxylamine are human metabolites of the industrial and environmental pollutant and bladder carcinogen 2-methoxyaniline (o-anisidine). The latter one is also a human metabolite of another pollutant and bladder carcinogen, 2-methoxynitrobenzene (o-nitroanisole). Here, we investigated the ability of rat hepatic microsomes to metabolize these metabolites. N-(2-methoxyphenyl)hydroxylamine is metabolized by rat hepatic microsomes to o-aminophenol and predominantly o-anisidine, the parent carcinogen from which N-(2-methoxyphenyl)hydroxylamine is formed. In addition, two N-(2-methoxyphenyl)hydroxylamine metabolites, whose exact structures have not been identified as yet, were generated. On the contrary, no metabolites were found to be formed from o-aminophenol by rat hepatic microsomes. Whereas N-(2-methoxyphenyl)hydroxylamine is responsible for formation of three deoxyguanosine adducts in DNA, o-aminophenol seems to be a detoxication metabolite of N-(2-methoxyphenyl)hydroxylamine and/or a parental carcinogen, o-anisidine; no o-aminophenol-derived DNA adducts were found after its reaction with microsomal cytochromes P450 and peroxidases.
Pt nanoparticles entrapped in ordered mesoporous carbons: An efficient catalyst for the liquid-phase hydrogenation of nitrobenzene and its derivatives
Li, Junrui,Li, Xiaohong,Ding, Yue,Wu, Peng
, p. 1995 - 2003 (2015)
Pt nanoparticles entrapped in ordered mesoporous CMK-3 carbons with p6mm symmetry were prepared using a facile impregnation method, and the resulting materials were characterized using X-ray diffraction spectroscopy, N2 adsorption-desorption, s
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Brand,Kranz
, p. 154 (1927)
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DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles
Cai, Jingyu,Ding, Qiuping,Peng, Yiyuan,Song, Zhibin,Tan, Yuxing,Ye, Xiaoling,Yuan, Sitian
, p. 1485 - 1492 (2022/01/20)
A novel DMF-assisted radical cyclization of o-isocyanodiaryl ethers via 1,5-aryl migration has been developed for the synthesis of a series of 2-arylbenzoxazoles by the FeCl3/TBHP/Et3N catalytic system in DMF. However, N,N-dimethylbenzo[d]thiazole-2-carboxamide and N,N-dimethylbenzo[d]selenazole-2-carboxamide were obtained from the corresponding substrate 2-isocyanophenyl p-methoxyphenyl thioether and 2-isocyanodiphenyl selenoether under the same conditions. A possible mechanism may involve aryl 1,5-migration and DMF-assisted radical cyclization of o-isocyanodiaryl ethers.
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0111-0118; 0121, (2021/05/29)
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
