o-Anisidine CAS 90-04-0
Introduction：Basic information about o-Anisidine CAS 90-04-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
o-Anisidine Basic information
| Product Name: | o-Anisidine |
| Synonyms: | O-AMINOPHENOL METHYL ETHER;O-AMINOANISOLE;O-ANISIDINE;ORTHO ANISIDINE;O-METHOXYANILINE;2-Methoxy-1-aminobenzene;2-methoxy-benzenamin;2-Methoxybenzenamine |
| CAS: | 90-04-0 |
| MF: | C7H9NO |
| MW: | 123.15 |
| EINECS: | 201-963-1 |
| Product Categories: | Intermediates;Intermediates of Dyes and Pigments;amine;90-04-0 |
| Mol File: | 90-04-0.mol |
o-Anisidine Chemical Properties
| Melting point | 3-6 °C(lit.) |
| Boiling point | 225 °C(lit.) |
| density | 1.092 g/mL at 25 °C(lit.) |
| vapor pressure | <0.1 at 25 °C (NIOSH, 1994) |
| refractive index | n |
| Fp | 210 °F |
| storage temp. | Refrigerator |
| solubility | 14g/l |
| pka | 4.52(at 25℃) |
| form | Powder/Solid |
| color | Off-white |
| PH | 7.3 (1g/l, H2O, 20℃) |
| Water Solubility | 13 g/L (20 ºC) |
| Sensitive | Light Sensitive |
| Merck | 14,667 |
| BRN | 386210 |
| Henry's Law Constant | 1.25 at 25 °C (approximate - calculated from water solubility and vapor pressure) |
| Exposure limits | Potential occupational carcinogen. NIOSH REL: TWA 0.5 mg/m3, IDLH 50mg/m3; OSHA PEL: TWA 0.5 mg/m3; ACGIH TLV: TWA 0.1 ppm (adopted). |
| Dielectric constant | 5.2300000000000004 |
| Stability: | Stable. Incompatible with strong oxidizing agents, acid anhydrides, chloroformates, acids, some plastics, rubber. Air sensitive. |
| InChI | 1S/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3 |
| InChIKey | VMPITZXILSNTON-UHFFFAOYSA-N |
| SMILES | COc1ccccc1N |
| LogP | 1.180 |
| CAS DataBase Reference | 90-04-0(CAS DataBase Reference) |
| IARC | 2A (Vol. Sup 7, 73, 127) |
| NIST Chemistry Reference | Benzenamine, 2-methoxy-(90-04-0) |
| EPA Substance Registry System | o-Anisidine (90-04-0) |
Safety Information
| Hazard Codes | T,Xi |
| Risk Statements | 45-23/24/25-68 |
| Safety Statements | 53-45 |
| RIDADR | UN 2431 6.1/PG 3 |
| OEB | C |
| OEL | TWA: 0.5 mg/m3 [skin] |
| WGK Germany | 3 |
| RTECS | BZ5410000 |
| F | 8 |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29222200 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Carc. 1B Muta. 2 |
| Hazardous Substances Data | 90-04-0(Hazardous Substances Data) |
| Toxicity | Acute oral LD50 for rats 2,000 mg/kg, wild birds 422 mg/kg, mice 1,400 mg/kg, rabbits 870mg/kg (quoted, RTECS, 1985). |
| IDLA | 50 mg/m3 |
| Description | o-Anisidine was produced commercially in the United Statesfrom the 1920s until late 1950s. By 2009, worldwide only sixindustries manufactured o-anisidine, but none producedhydrochloride salt. o-Anisidine was available from 44 suppliers,including 20 US suppliers, and the hydrochloride salt wasavailable from eight suppliers, including five US suppliers. USimports of o-anisidine and its hydrochloride salt are reported inthe category ‘o-anisidines, p-anisidines, and p-phenetidine,’ andUS 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 tozero in 2007 and 2008, and exports ranged from zero to262 000 kg. Reports filed under the US EnvironmentalProtection Agency’s (EPA) Toxic Substances Control ActInventory Up Rule indicated that United States production plusimports 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 | 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. |
| Uses | In the preparation of azo dyes; corrosioninhibitor; chemical intermediate |
| Uses | It is primarily used as a chemical intermediate in the productionof pigments, dyes, pharmaceuticals, and fragrances.o-Anisidine hydrochloride is used as a chemical intermediate inthe production of numerous azo and triphenylmethane dyesand pigments (e.g., C.I. direct red 72, disperse orange 29, directyellow 44, direct red 24, and acid red 4); in the production ofpharmaceuticals, including the expectorant guaiacol; asa corrosion inhibitor for steel; and as an antioxidant for polymercaptanresins. |
| Definition | 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. |
| 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 absorbedthrough the skin. Possible carcinogen. |
| Health Hazard | o-Anisidine was carcinogenic inexperimental animals. |
| Fire Hazard | o-Anisidine is combustible. |
| Safety Profile | Confirmed carcinogen.Moderately toxic by ingestion. Mutation datareported. When heated to decomposition itemits toxic fumes of NOx. |
| Potential Exposure | Anisidines are used in the manufactureof azo dyes; pharmaceuticals; textile-processing chemicalsIncompatibilities: 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 coatingsand some forms of plastic and rubber. |
| Carcinogenicity | o-Anisidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals. |
| Environmental fate | Biological. o-Anisidine should be biodegradable according to OECD guidelines (Brown andLabouerer (1983).Chemical/Physical. At influent concentrations (pH 3.0) of 10, 1.0, 0.1, and 0.01 mg/L, the GACadsorption capacities were 52, 20, 7.8, and 3.0 mg/g, respectively. At pHs 7 and 9, the GACadsorption capacities were 110, 50, 23, and 10 mg/g at influent concentrations of 10, 1.0, 0.1, and0.01 mg/L, respectively (Dobbs and Cohen, 1980). |
| Shipping | UN2431 Anisidines, Hazard Class: 6.1; Labels:6.1-Poisonous materials |
| 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, andit forms two o-anisidine–DNA adducts with DNA. It causesDNA damage by a metabolite in the presence of metals suchas Cu(II). It can also cause Cu(II)-mediated oxidative DNAdamage. |
| Waste Disposal | Dissolve in combustible solvent(alcohols, benzene, etc.) and spray solution into furnaceequipped with afterburner and scrubber, or burn spillresidue on sand and soda ash absorbent in a furnace. |
o-Anisidine Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Methanol-->Iron-->Sodium sulfide-->2-Nitrochlorobenzene-->2-Nitrophenol |
| Preparation Products | Vanillin-->Guaiacol-->XANTHURENIC ACID-->NAPHTHOL AS-BI PHOSPHATE-->5-BROMO-8-METHOXY-2-METHYL-QUINOLINE-->2-Methoxy-4-nitroaniline-->2-METHOXYBENZENETHIOL-->4-AMINO-3-METHOXYPHENYLBORONIC ACID, PINACOL ESTER-->Fast Scarlet RC Base-->o-Acetoacetaniside-->N-(2-Methoxyphenyl)acetamide-->1-(2-Methoxyphenyl)piperazine-->1-(2-Methoxyphenyl)piperazine hydrobromide-->3,4-DIHYDRO-8-HYDROXY-4-OXOQUINOLINE-3-CARBOXYLIC ACID-->Disperse Orange 29-->2'-Methylacetoacetanilide-->N-(4-AMINO-2-METHOXYPHENYL)ACETAMIDE-->Naphthol AS-OL-->METOXADIAZONE-->3,8-DIMETHYL-1,10-PHENANTHROLINE-->4-HYDROXY-8-METHOXYQUINOLINE-3-CARBOXYLIC ACID-->5-Chloro-2-methoxyaniline-->2-Fluoroanisole-->SIRIUS YELLOW GC-->disodium 3,3'-[carbonylbis[imino(3-methoxy-4,1-phenylene)azo]]dibenzoate-->Fast Red ITR-->2-Methoxyphenyl isocyanate-->4-HYDROXY-8-METHOXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER-->N-(2-METHOXY-4-NITROPHENYL)ACETAMIDE-->Reactive Yellow KE-4RN-->FAST RED B SALT-->Benzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul-->2-Methoxybenzonitrile-->FAST RED SALT ITR-->Naphtanilide EL |
