ChemicalBook > Product Catalog > Organic Chemistry > Ethers and derivatives > Ethers, ether-alcohols, ether phenol derivatives > o-Anisidine
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
- Flash point:210 °F
- storage temp. Refrigerator
- solubility 14g/l
- pka4.52(at 25℃)
- form Powder/Solid
- color Off-white
- PH7.3 (1g/l, H2O, 20℃)
- Water Solubility 13 g/L (20 ºC)
- Sensitive Light Sensitive
- Merck 14,667
- BRN 386210
- Henry's Law Constant1.25 at 25 °C (approximate - calculated from water solubility and vapor pressure)
- Exposure limitsPotential occupational carcinogen. NIOSH REL: TWA 0.5 mg/m3, IDLH 50 mg/m3; OSHA PEL: TWA 0.5 mg/m3; ACGIH TLV: TWA 0.1 ppm (adopted).
- Stability:Stable. Incompatible with strong oxidizing agents, acid anhydrides, chloroformates, acids, some plastics, rubber. Air sensitive.
- CAS DataBase Reference90-04-0(CAS DataBase Reference)
- IARC2A (Vol. Sup 7, 73, 127)
- NIST Chemistry ReferenceBenzenamine, 2-methoxy-(90-04-0)
- EPA Substance Registry Systemo-Anisidine (90-04-0)
- Hazard Codes T,Xi
- Risk Statements 45-23/24/25-68
- Safety Statements 53-45
- RIDADR UN 2431 6.1/PG 3
- WGK Germany 3
- RTECS BZ5410000
- F 8
- TSCA Yes
- HazardClass 6.1
- PackingGroup III
- HS Code 29222200
- Hazardous Substances Data90-04-0(Hazardous Substances Data)
- ToxicityAcute oral LD50 for rats 2,000 mg/kg, wild birds 422 mg/kg, mice 1,400 mg/kg, rabbits 870 mg/kg (quoted, RTECS, 1985).
o-Anisidine Usage And Synthesis
- Chemical PropertiesAnisidine 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 propertiesColorless, yellow to reddish liquid with an amine-like odor. Becomes brown on exposure to air.
- UsesSimilar 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.
- UsesIn the preparation of azo dyes; corrosion inhibitor; chemical intermediate
- Synthesis Reference(s)Tetrahedron Letters, 24, p. 4733, 1983 DOI: 10.1016/S0040-4039(00)86242-5
- General DescriptionClear, yellowish to reddish or brown liquid with an amine (fishy) odor.
- Air & Water Reactionso-Anisidine darkens on exposure to air. Insoluble in water.
- Reactivity Profileo-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. .
- HazardStrong irritant. Toxic when absorbed through the skin. Possible carcinogen.
- Health Hazardo-Anisidine was carcinogenic in experimental animals.
- Fire Hazardo-Anisidine is combustible.
- Safety ProfileConfirmed carcinogen. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
- Potential ExposureAnisidines 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.
- Carcinogenicityo-Anisidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals.
- Environmental FateBiological. 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).
- ShippingUN2431 Anisidines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
- Purification MethodsIt 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.]
- Waste DisposalDissolve 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.
o-Anisidine Preparation Products And Raw materials
- Preparation ProductsVanillinGuaiacolXANTHURENIC ACIDNAPHTHOL AS-BI PHOSPHATE5-BROMO-8-METHOXY-2-METHYL-QUINOLINE2-Methoxy-4-nitroaniline2-METHOXYBENZENETHIOL4-AMINO-3-METHOXYPHENYLBORONIC ACID, PINACOL ESTERFast Scarlet RC Baseo-AcetoacetanisideN-(2-Methoxyphenyl)acetamide1-(2-Methoxyphenyl)piperazine1-(2-Methoxyphenyl)piperazine hydrobromide3,4-DIHYDRO-8-HYDROXY-4-OXOQUINOLINE-3-CARBOXYLIC ACIDDisperse Orange 292'-MethylacetoacetanilideN-(4-AMINO-2-METHOXYPHENYL)ACETAMIDENaphthol AS-OLMETOXADIAZONE3,8-DIMETHYL-1,10-PHENANTHROLINE4-HYDROXY-8-METHOXYQUINOLINE-3-CARBOXYLIC ACID5-Chloro-2-methoxyaniline2-FluoroanisoleSIRIUS YELLOW GCdisodium 3,3'-[carbonylbis[imino(3-methoxy-4,1-phenylene)azo]]dibenzoateFast Red ITR2-Methoxyphenyl isocyanate4-HYDROXY-8-METHOXY-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTERN-(2-METHOXY-4-NITROPHENYL)ACETAMIDEReactive Yellow KE-4RNFAST RED B SALTBenzoic 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-sul2-MethoxybenzonitrileFAST RED SALT ITRNaphtanilide EL
- Raw materialsSodium hydroxideMethanolIronSodium sulfide2-Nitrochlorobenzene2-Nitrophenol
- Aniline-2-sulfonic acid 2,4-DIAMINOANISOLE 4-Aminoveratrole AMINO ACIDS Azoic Diazo Component 1 4-(Trifluoromethoxy)aniline anisidine 2-Aminobenzaldehyde Betaine 3-Ethoxyaniline Anthranilic acid Guaiacol 2-Aminobenzyl alcohol 2-(Trifluoromethoxy)aniline 2-Nitroaniline Methyl anthranilate o-Toluidine ALTRENOGEST
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