536-90-3 Usage
Description
m-Anisidine, a monosubstituted aniline, is a highly poisonous compound that exists in various isomers, including ortho-, meta-, and para-anisidine. It appears as a pale yellow oily liquid or dark red liquid and has a characteristic amine (fishy) odor. It is soluble in alcohol, ether, benzene, and dilute acid, and slightly soluble in water.
Uses
Used in Corrosion Inhibition:
m-Anisidine is used as a corrosion inhibitor for aluminum, copper, and other metals in acidic solutions. Its effectiveness in preventing the corrosion of these metals makes it a valuable additive in various industrial applications.
Used in Chemical Synthesis:
m-Anisidine is utilized in the synthesis of N-substituted-3-chloro-2-azetidinones, which are potential anthelmintic agents. These compounds can be used to combat parasitic worm infections.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, m-Anisidine is employed in the rhodium-catalyzed synthesis of indoles and copper-catalyzed synthesis of benzimidazoles. These compounds have various applications in the development of new drugs and pharmaceuticals.
Used in Dye Preparation:
m-Anisidine is also used in the preparation of azocalix[4]arene dyes, which are important for various applications in the dye and pigment industry.
Used in Organocatalytic Asymmetric Three-Component Cyclization:
m-Anisidine has been found to exhibit the best enantioselectivity of 97% ee in the organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1,3-Dicarbonyl Compounds. This high enantioselectivity makes it a valuable compound in the synthesis of chiral molecules with potential applications in various industries.
Used in Second-Harmonic Generation Activities:
The x-ray crystal-structures of the complexes of l-tartaric acid with m-anisidine and p-toluidine have provided evidence for the control of second-harmonic generation activities. This makes m-Anisidine a potential candidate for applications in nonlinear optics and photonics.
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).
Synthesis Reference(s)
The Journal of Organic Chemistry, 22, p. 333, 1957 DOI: 10.1021/jo01354a610Tetrahedron Letters, 24, p. 4121, 1983 DOI: 10.1016/S0040-4039(00)88277-5
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 536-90-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 6 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 536-90:
(5*5)+(4*3)+(3*6)+(2*9)+(1*0)=73
73 % 10 = 3
So 536-90-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO/c1-2-10-8-5-3-4-7(9)6-8/h3-6H,2,9H2,1H3
536-90-3Relevant articles and documents
Ullmann reaction of picryl bromide in the presence of ultrasound
Nelson,Adolph
, p. 293 - 305 (1991)
Ultrasonic irradiation was found to promote the Ullman coupling of picryl bromide at or below room temperature. In the presence of excess copper, a long-lived intermediate is formed that is quenched upon work-up affording variable mixtures of trinitrobenzene and picric acid.
THE PLATINUM CATALYZED REDUCTION OF NITROARENES TO AMINOARENES WITH CARBON MONOXIDE AND WATER
Watanabe, Yoshihisa,Tsuji, Yasushi,Ohsumi, Tatsuya,Takeuchi, Ryo
, p. 4121 - 4122 (1983)
Nitroarenes were readily transformed to aminoarenes in excellent yields under mild conditions with carbon monoxide and water in the presence of a platinum catalyst.Triethylamine, SnCl4 and PPh3 are essential for the high catalytic activity.Nitroarenes are reduced chemoselectively by this procedure.
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0111-0118; 0120, (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.
Efficient strategy for interchangeable roles in a green and sustainable redox catalytic system: IL/PdII-decorated SBA-15 as a mesoporous nanocatalyst
Sadeghi, Samira,Karimi, Meghdad,Radfar, Iman,Gavinehroudi, Reza Ghahremani,Saberi, Dariush,Heydari, Akbar
, p. 6682 - 6692 (2021/04/22)
Time and again, SBA-15-based composites as mesoporous materials and the incorporation of transition metals in them have been attracting dramatic attention in the field of catalysis due to their remarkable features. In this paper, the activity of SBA-15 supported ionic liquid-Pd(ii) has been investigated in the catalytic transfer hydrogenation of nitroarenes with formic acid as a hydrogen donor at room temperature in water medium, and the oxidation of benzyl alcohols to benzaldehyde derivatives under atmospheric oxygen at high temperature. This novel nanocatalyst was characterized by FT-IR, SA-XRD, BET, BJH, TGA, FE-SEM, TEM, and ICP as the most commonplace techniques for analyzing its characteristics to be revealed as truth. Furthermore, the EDX analysis illustrates the grafting of the ionic liquid-Pd(ii) into SBA-15. The catalyst showed high stability under reaction conditions, and can be recovered and reused for at least 15 and 6 reaction runs in oxidation and reduction reactions, respectively.