| | m-Anisidine Basic information |
| | m-Anisidine Chemical Properties |
| Melting point | −1-1 °C(lit.) | | Boiling point | 251 °C(lit.) | | density | 1.096 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.581(lit.) | | Fp | >230 °F | | storage temp. | 2-8°C | | solubility | 18g/l | | pka | 4.23(at 25℃) | | form | Liquid | | color | Clear yellow to brown | | Water Solubility | <0.1 g/100 mL at 19 ºC | | Sensitive | Light Sensitive | | Merck | 14,667 | | BRN | 386119 | | InChIKey | NCBZRJODKRCREW-UHFFFAOYSA-N | | LogP | 0.930 | | CAS DataBase Reference | 536-90-3(CAS DataBase Reference) | | NIST Chemistry Reference | Benzenamine, 3-methoxy-(536-90-3) | | EPA Substance Registry System | m-Anisidine (536-90-3) |
| | m-Anisidine Usage And Synthesis |
| Chemical Properties | Light yellow oily liquid with have characteristic amine (fishy) odors. soluble in alcohol, ether, benzene and dilute acid, slightly soluble in water. Anisidine exists as ortho-, meta-, and paraisomers. | | Uses | m-Anisidine is a highly poisonous monosubstituted aniline used as corrosion inhibitorsfor aluminum, copper and other metals in acidic solutions. | | Uses | The unusually large amount of dibromo product produced upon bromination of m-anisidine may be attributed to the two doubly activeated positions. The best enantioselectivity of 97 % ee was observed for the reaction of m-anisidine in organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1, 3-Dicarbonyl Compounds. Evidence for the control of 2nd-harmonic generation activities from the x-ray crystal-structures of the complexes of l-tartaric acid with m-anisidine and p-toluidine was determined. | | Application | m-Anisidine is used in:
The synthesis of N-substituted-3-chloro-2-azetidinones, which are potential anthelmintic agents.
Rhodium-catalyzed synthesis of indoles and copper-catalyzed synthesis of benzimidazoles.
In the preparation of azocalix[4]arene dyes. | | Preparation | m-Aminoanisole is synthesized by reduction of m-nitrophenol after methylation on the hydroxyl group.
A mixture of 35 g. (0.23 mole) of m-nitroanisole (p. 213), 110 ml. of methanol, and 7.5 ml. of concentrated hydrochloric acid is stirred and heated to boiling. Forty-two grams (0.75 gram atom) of iron filings is added in small portions over a 1-hour period, and refluxing and stirring are continued for 5 additional hours. The mixture is made strongly alkaline with sodium hydroxide and steam-distilled, the methanol which first distils over being collected separately. The remainder of the distillate is extracted with ether; the ethereal solu-tion is dried over anhydrous sodium sulfate and distilled. m-Anisidine (23.2 g. or 80%) is collected at 125°/13 mm.
Reference: J. Chem. Soc, 1934, 1420; J. Chem. Soc, 127, 494 (1925). | | Definition | ChEBI: 3-Methoxyaniline is a substituted aniline and an aromatic ether. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 22, p. 333, 1957 DOI: 10.1021/jo01354a610
Tetrahedron Letters, 24, p. 4121, 1983 DOI: 10.1016/S0040-4039(00)88277-5 | | General Description | M-anisidine appears as pale yellow oily liquid or dark red liquid. (NTP, 1992) | | Air & Water Reactions | m-Anisidine may be sensitive to prolonged exposure to air and light. Insoluble in water. | | Reactivity Profile | m-Anisidine is incompatible with strong oxidizers. m-Anisidine is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. | | Fire Hazard | m-Anisidine is probably combustible. | | Safety Profile | Moderately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic vapors of NOx. | | Potential Exposure | 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. | | Shipping | UN2431 Anisidines, Hazard Class: 6.1; Labels:
6.1-Poisonous materials | | Purification Methods | o-Isomer impurity can be removed by steam distillation. Another possible impurity is the precursor 3-nitroanisole which can be removed as for the preceding o-isomer and fractionating using an efficient column. It is a yellow liquid. [Gilman & Kyle J Am Chem Soc 74 3027 1952, Bryson J Am Chem Soc 82 4858 1960, Kadaba & Massie J Org Chem 22 333 1957, Beilstein 13 IV 953.] | | Waste Disposal | 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. |
| | m-Anisidine Preparation Products And Raw materials |
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