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Cas Database

536-90-3

536-90-3

Identification

  • Product Name:m-Anisidine

  • CAS Number: 536-90-3

  • EINECS:208-651-4

  • Molecular Weight:123.155

  • Molecular Formula: C7H9NO

  • HS Code:29222200

  • Mol File:536-90-3.mol

Synonyms:1-Amino-3-methoxybenzene;3-Aminoanisole;3-Methoxyaniline;3-Methoxybenzenamine;3-Methoxyphenylamine;NSC 7631;m-Aminoanisole;m-Aminomethoxybenzene;m-Anisylamine;m-Methoxyaniline;Benzenamine, 3-methoxy-;

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Safety information and MSDS view more

  • Pictogram(s):VeryT+, DangerousN, HarmfulXn

  • Hazard Codes:Xn,N,T+

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Other symptoms may include headaches and cyanosis. It can cause dizziness and an increase in red blood cell Heinz bodies. Vertigo and an increase in sulfhemoglobin may occur. Drowsiness has been reported. The onset of symptoms may be delayed 2 to 4 hours or longer. Symptoms of exposure to a related compound include methemoglobinemia, skin sensitization, corneal damage, and liver and kidney damage. ACUTE/CHRONIC HAZARDS: This compound is very toxic by ingestion, inhalation and skin contact. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. It is readily absorbed through the skin. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode. /Anisidines/ This chemical is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Spill handling: Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area of spill or leak. Cover with sand and soda ash (9:1). After mixing, collect material in the most convenient and safe manner and deposit in sealed containers. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. It may be necessary to contain and dispose of this chemical as a hazardous waste. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. /Anisidines/

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Well closed. Separated from food and feedstuffs and strong oxidants.Store in tightly closed containers in a cool, dark, well-ventilated area. Protect against sunlight and strong oxidizers. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard. A regulated, marked area should be established where this chemical is handled, used, or stored ... /Anisidines/

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:m-Anisidine
  • Packaging:25g
  • Price:$ 403
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  • Manufacture/Brand:TRC
  • Product Description:m-Anisidine
  • Packaging:25g
  • Price:$ 120
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  • Manufacture/Brand:TCI Chemical
  • Product Description:m-Anisidine >98.0%(GC)(T)
  • Packaging:500g
  • Price:$ 104
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  • Manufacture/Brand:TCI Chemical
  • Product Description:m-Anisidine >98.0%(GC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:m-Anisidine >98.0%(GC)(T)
  • Packaging:100g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Methoxyaniline
  • Packaging:25 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Methoxyaniline
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:m-Anisidine 97%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:m-Anisidine 97%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:m-Anisidine 97%
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Relevant articles and documentsAll total 197 Articles be found

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.

Reduction of aromatic nitro compounds under solvent-free conditions using alumina-supported hydrazine/FeNH4(SO4)2· 12H2O

Zhang, Chang-Rui,Wang, Yu-Lu,Wang, Jin-Ye

, p. 569 - 570 (2004)

Aromatic nitro compounds were easily reduced to the corresponding amino compounds with hydrazine hydrate supported on alumina in the presence of FeNH4(SO4)2·12H2O.

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.

Selective hydrodeoxygenation of acetophenone derivatives using a Fe25Ru75@SILP catalyst: a practical approach to the synthesis of alkyl phenols and anilines

Bordet, Alexis,Goclik, Lisa,Leitner, Walter,Walschus, Henrik

supporting information, p. 2937 - 2945 (2022/04/07)

A versatile synthetic pathway for the production of valuable alkyl phenols and anilines has been developed based on the selective hydrodeoxygenation of a wide range of hydroxy-, amino-, and nitro-acetophenone derivatives as readily available substrates. Bimetallic iron ruthenium nanoparticles immobilized on an imidazolium-based supported ionic liquid phase (Fe25Ru75@SILP) act as highly active and selective catalysts for the deoxygenation of the side-chain without hydrogenation of the aromatic ring. The catalytic system allows operation under continuous flow conditions with high robustness and flexibility as demonstrated for the alternating conversion of 3′,5′-dimethoxy-4′-hydroxyacetophenone and 4′-hydroxynonanophenone as model substrates.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.

, p. 2895 - 2906 (2021/02/27)

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

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.

Fabrication of palladium nanocatalyst supported on magnetic eggshell and its catalytic character in the catalytic reduction of nitroarenes in water

?al??kan, Melike,Akay, Sema,Baran, Talat,Kayan, Berkant

, (2021/07/21)

Aromatic nitro compounds, which have good solubility in water, are highly toxic and non-biodegradable are one of the most important industrial pollutants and have negative effects on human health, aquatic life and the environment. Therefore, the elimination of these harmful organic compounds has become an issue of great importance. For this, in this study we have developed a palladium nanocatalyst supported on Fe3O4-coated eggshell and characterized by FT-IR, XRD, XPS, FE-SEM, TG/DTG, BET, TEM and EDS techniques (Pd-Fe3O4-ES). Also, the quantitative analysis of Pd was determined using ICP-OES. The catalytic behavior of the designed Pd-Fe3O4-ES nanocatalyst was investigated against the catalytic reduction of several highly toxic nitro compounds using NaBH4 in water at room temperature. The progress of the reduction was followed using high performance liquid chromatography (HPLC). The catalytic studies revealed that the nitro compounds were converted into the desired amines by the Pd-Fe3O4-ES nanocatalyst using a very low dose of catalyst (15 mg) and short-duration reactions (81–360 s) in aqueous medium at ambient temperature. Furthermore, the Pd-Fe3O4-ES nanocatalyst showed good catalytic stability by retaining its activity after the fifth catalytic run.

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

-

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.

Process route upstream and downstream products

Process route

C<sub>11</sub>H<sub>17</sub>NO<sub>3</sub>Si
104824-45-5

C11H17NO3Si

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

isopropoxytrimethylsilane
1825-64-5

isopropoxytrimethylsilane

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

Conditions
Conditions Yield
With lithium chloride; Kinetics; Thermodynamic data; Product distribution; ΔH excit;
3-nitroanisole
555-03-3

3-nitroanisole

Conditions
Conditions Yield
With isopropyl alcohol; potassium hydroxide; for 0.133333h; regioselective reaction; Microwave irradiation;
98%
With hydrogen; In ethanol; water; at 25 ℃; for 6h; under 11251.1 Torr; chemoselective reaction;
98%
With nickel(II) oxide; ethanol; potassium hydroxide; for 0.183333h; Microwave irradiation; sealed vessel;
97%
With BiFeO3; isopropyl alcohol; potassium hydroxide; for 0.166667h; Microwave irradiation;
97%
With sodium tetrahydroborate; water; nickel; at 20 ℃; for 1.33333h;
96%
With carbon monoxide; water; bis(triphenylphosphine)platinum(II) dichloride; water; tin(IV) chloride; triethylamine; In 1,4-dioxane; at 80 ℃; for 4h; under 45600 Torr;
95%
With zinc; hydrazinium monoformate; In water; for 0.0333333h;
95%
With hydrazine hydrate; zinc; In methanol; at 20 ℃; for 0.0666667h;
95%
With sodium sulfide; tetrabutylammomium bromide; In water; toluene; at 80 ℃; for 1h;
95.7%
With hydrogenchloride; iron; In ethanol;
95.5%
With sodium tetrahydroborate; water; at 20 ℃; for 0.00194444h; Reagent/catalyst; Catalytic behavior; Green chemistry;
95%
With isopropyl alcohol; potassium hydroxide; for 0.3h; chemoselective reaction; Microwave irradiation;
94%
With glycerol; potassium hydroxide; at 130 ℃; for 0.166667h; Sonication; Microwave irradiation;
94%
3-nitroanisole; In water; for 0.0833333h;
With sodium tetrahydroborate; In water; at 65 ℃; for 0.05h; Catalytic behavior;
93%
With chlorobis(cyclooctene)rhodium(I) dimer; In N,N-dimethyl-formamide; at 120 ℃; for 24h; pH=2.25; Inert atmosphere;
93%
With glycerol; potassium hydroxide; at 80 ℃; for 3.5h;
92%
With sodium tetrahydroborate; In tetrahydrofuran; water; at 20 ℃; for 3h; Catalytic behavior; Green chemistry;
92%
With water; iron; at 210 ℃; for 2h;
91%
With hydrazine; Montmorillonite; In ethanol; for 8h; Heating;
90%
With [Co(κS,N-4-(trifluoromethyl)pyrimidine-2-thiolate)3]; methylhydrazine; In methanol; at 70 ℃; for 4h; Sealed tube;
90%
With iron; acetic acid; In ethanol; water; at 30 ℃; for 1h; sonication;
89%
With hydrogen; In water; at 25 ℃; for 14h; chemoselective reaction; Green chemistry;
87%
3-nitroanisole; In methanol; water; at 20 ℃;
With sodium tetrahydroborate; In methanol; water; at 50 ℃; for 2h;
86%
With 1 wt.%Ir/ZrO2; hydrogen; In ethanol; at 24.84 ℃; under 15001.5 Torr; chemoselective reaction; Kinetics; Autoclave;
84%
With sodium tetrahydroborate; copper(II) oxide; In water; at 30 ℃; for 1.7h; Catalytic behavior;
74%
With hydrazine hydrate; In ethanol; for 24h; chemoselective reaction; Irradiation;
71%
With aluminum oxide; ammonium ferric sulfate; hydrazine; for 0.0666667h; microwave irradiation;
65%
With samarium; iodine; ammonium chloride; In tetrahydrofuran; water; at 20 ℃; for 5h;
62%
In water; at 31 - 35 ℃; for 72h; reduction with baker's yeast (Saccharomyces cerevisiae);
25%
With hydrogenchloride; ethanol; iron;
With ethanol; nickel; at 95 ℃; under 68400 Torr; Hydrogenation;
With hydrogenchloride; tin;
With hydrogenchloride; zinc;
With sodium disulfide;
With carbon monoxide; water; tin(IV) chloride; triethylamine; bis(triphenylphosphine)platinum(II) dichloride; In 1,4-dioxane; at 80 ℃; for 4h; under 44130.5 Torr;
100 % Chromat.
With sodium hydroxide; In methanol; at 25 ℃; Yield given; electrochemical reduction;
With hydrogen; palladium on activated charcoal; In methanol;
With potassium hydroxide; acetophenone; In isopropyl alcohol; for 22h; Heating;
88 % Chromat.
With nickel; isopropyl alcohol; at 50 ℃; for 2.5h; Yield given;
With carbon monoxide; water; sodium formate; (Ph4C4CO)(CO)3Ru; In tetrahydrofuran; at 105 ℃; for 22h; under 25857.4 Torr;
100 % Chromat.
With morpholine; hydrogen; {Co(II)(DH)2(H2O)2}; In acetone; at 20 ℃; under 750.06 Torr; Rate constant;
With hydrogenchloride; tin(ll) chloride; In ethanol; water; at 30 ℃; Rate constant;
With [Pd(HBOADO)]Cl2; hydrogen; In water; N,N-dimethyl-formamide; for 0.333333h;
78 %Spectr.
With hydrogenchloride; indium; In water; at 20 ℃; for 0.166667h;
With hydrogenchloride; iron; In ethanol; water; Reflux;
With carbon dioxide; hydrogen; at 50 ℃; for 0.166667h; under 18751.9 - 90009 Torr; Supercritical conditions;
With carbon dioxide; hydrogen; at 50 ℃; for 0.166667h; under 105011 Torr; chemoselective reaction; Supercritical conditions;
With palladium on activated charcoal; sodium n-propoxide; In propan-1-ol; at 49.84 ℃; for 3h;
93 %Chromat.
With hexarhodium hexadecacarbonyl; carbon monoxide; In water; toluene; at 80 ℃; for 6h; under 7600.51 Torr; chemoselective reaction; Autoclave;
99 %Chromat.
With sodium tetrahydroborate; water; at 20 ℃; for 3h; Inert atmosphere; Green chemistry;
92 %Chromat.
With hydrogen; In ethanol; at 25 ℃; for 2h; under 760.051 Torr;
> 99 %Chromat.
With hydrogen; In ethanol; at 24.84 ℃; under 15001.5 Torr; chemoselective reaction; Kinetics;
With C25H25ClF3IrN4(1+)*F6P(1-); potassium hydroxide; In isopropyl alcohol; at 80 ℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;
With hydrogen; palladium; In ethyl acetate; at 120 ℃; under 15001.5 Torr; Temperature; Solvent; Pressure; Catalytic behavior; Flow reactor;
With sodium tetrahydroborate; In diethyl ether; water; at 25 ℃; for 4h; Inert atmosphere;
91 %Chromat.
With ammonium formate; In tetrahydrofuran; water; at 120 ℃; for 12h; chemoselective reaction; Inert atmosphere; Schlenk technique; Green chemistry;
With hydrogen; In water; at 80 ℃; for 12h; under 760.051 Torr; chemoselective reaction;
98 %Chromat.
With sodium tetrahydroborate; In methanol; at 25 ℃; for 2h; Inert atmosphere; Schlenk technique;
With sodium tetrahydroborate; In ethanol; water; at 20 ℃; for 1h;
With hydrogen; In ethanol; at 100 ℃; for 2h; under 7500.75 Torr;
With hydrogen; In ethanol; at 100 ℃; for 2h; under 7500.75 Torr;
With hydrogen; In ethanol; at 100 ℃; for 2h; under 7500.75 Torr;
With formic acid; In water; at 20 ℃; for 5h;
3-nitroanisole; at 20 ℃; for 0.0333333h; Green chemistry;
With sodium tetrahydroborate; In water; at 20 ℃; for 0.0477778h; Green chemistry;
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

Conditions
Conditions Yield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 5h; Inert atmosphere;
99%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide; In dimethyl sulfoxide; at 80 ℃; for 23h; Inert atmosphere;
93%
With ammonium hydroxide; copper(l) iodide; diethylenetriaminopentaacetic acid; potassium hydroxide; In water; at 100 ℃; for 12h; Sealed tube;
90%
With potassium phosphate; N2,N2'-diisopropyloxalohydrazide; tetrabutylammomium bromide; ammonia; copper(II) oxide; In water; at 60 ℃; for 24h;
89%
With trimethylsilylazide; copper; ethanolamine; In N,N-dimethyl acetamide; at 95 ℃; for 24h; Inert atmosphere;
89%
With [N,N'-bis(5-sulfonatosalicylidene)-1,2-diaminoethane]copper disodium salt; ammonia; sodium hydroxide; In water; at 120 ℃; for 12h; sealed tube;
88%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide; In dimethyl sulfoxide; at 110 ℃; for 24h; Inert atmosphere; Sealed tube;
87%
With copper(l) iodide; ammonia; potassium carbonate; In water; dimethyl sulfoxide; at 100 ℃; for 24h;
87%
With copper acetylacetonate; ammonium hydroxide; caesium carbonate; acetylacetone; In water; N,N-dimethyl-formamide; at 90 ℃; for 24h; Inert atmosphere;
85%
With ammonia; caesium carbonate; copper acetylacetonate; acetylacetone; In water; N,N-dimethyl-formamide; at 90 ℃; for 24h; Product distribution / selectivity; Inert atmosphere; Sealed tube;
85%
With oxalic acid hydrazide; ammonium hydroxide; tetrabutylammomium bromide; potassium carbonate; 2,5-hexanedione; copper(II) oxide; In water; at 90 ℃; for 1.33333h;
85%
With diethylenetriaminopentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide; In water; at 100 ℃; for 12h;
85%
With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline; In dimethyl sulfoxide; at 50 ℃; for 24h;
83%
With trimethylsilylazide; copper; ethanolamine; In N,N-dimethyl acetamide; at 95 ℃; for 24h; Inert atmosphere;
81%
With copper(l) iodide; ammonia; sodium phosphate; In water; at 100 ℃; for 24h;
80%
3-methoxyphenyl bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;
With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h; Inert atmosphere;
With water; sodium hydroxide; hydroxylamine-O-sulfonic acid; In tetrahydrofuran; hexane; at 20 ℃; for 16h; Inert atmosphere;
78%
3-methoxyphenyl bromide; With magnesium; In tetrahydrofuran; Inert atmosphere;
With C10H17NO; In tetrahydrofuran; toluene; at -78 ℃; for 2h; Inert atmosphere;
With ammonium chloride; In tetrahydrofuran; water; toluene; Inert atmosphere;
67%
3-methoxyphenyl bromide; With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate; In water; acetone; at 90 ℃; for 0.166667h;
With ammonia; In water; acetone; at 90 ℃; for 30h;
57%
With ammonium hydroxide; copper(ll) sulfate pentahydrate; potassium carbonate; sodium L-ascorbate; In dimethyl sulfoxide; glycerol; at 100 ℃; for 8h;
40%
Multi-step reaction with 2 steps
1: 94 percent / rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; t-BuONa / Pd2(dba)3 / toluene / 80 °C
2: 63 percent / aq. HCl / tetrahydrofuran / 20 °C
With hydrogenchloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); In tetrahydrofuran; toluene; 1: Buchwald-Hartwig amination;
With copper(l) iodide; ascorbic acid; In ammonia; at 100 ℃; for 18h; liquid NH3;
91 %Chromat.
With sodium azide; copper; L-proline; In water; dimethyl sulfoxide; at 150 ℃; for 0.583333h; under 37503.8 Torr; chemoselective reaction; Flow reactor;
N'-(3-methoxy-phenyl)-N,N-dibenzyl-formamidine

N'-(3-methoxy-phenyl)-N,N-dibenzyl-formamidine

Conditions
Conditions Yield
With hydrogen; palladium dihydroxide; In water; tert-butyl alcohol; under 3620.04 Torr; Ambient temperature;
90%
With hydrogen; palladium dihydroxide; In water; tert-butyl alcohol; at 20 ℃; for 5h; under 2844.31 Torr;
90%
1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

Conditions
Conditions Yield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;
99%
With C43H63ClFeNiP2; ammonia; sodium t-butanolate; In 1,4-dioxane; toluene; at 100 ℃; for 16h; Reagent/catalyst; Inert atmosphere;
91%
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate; at 100 - 110 ℃; for 12h;
88%
With bis(1,5-cyclooctadiene)nickel (0); (R)-1-[(Sp)-2-(dicyclohexylphosphanyl)ferrocenyl]ethyldicyclohexylphosphane; ammonia; sodium t-butanolate; In 1,4-dioxane; toluene; at 110 ℃; for 16h; Sealed tube;
potassium 3-methoxyphenyltrifluoroborate

potassium 3-methoxyphenyltrifluoroborate

Conditions
Conditions Yield
With sodium hydroxide; hydroxylamine-O-sulfonic acid; In water; acetonitrile; at 100 ℃; for 0.25h; Microwave irradiation;
76%
3-methoxyphenyl azide
3866-16-8

3-methoxyphenyl azide

Conditions
Conditions Yield
With ammonium hydroxide; at 90 ℃; for 0.166667h;
98%
With zinc; In methanol; at 20 ℃; for 6h;
94%
With aluminium(III) iodide; In benzene; for 0.166667h; Heating;
93%
3-methoxyphenyl azide; With hydrazine hydrate; for 0.166667h; Inert atmosphere;
for 12h; chemoselective reaction; Irradiation;
91%
With 1,3-diphenyl-disiloxane; triphenylphosphine; In toluene; at 23 ℃; for 24h; Reagent/catalyst; Solvent;
88%
With water; for 5h; chemoselective reaction; Inert atmosphere; UV-irradiation; Sealed tube;
88%
With (thermal decomposition); In decalin; at 141.3 ℃; Rate constant;
Multi-step reaction with 2 steps
1: 1,1'-diazenediyldicyclohexanecarbonitrile; tert-dodecanethiol / toluene / 4 h / 110 °C
2: H2O / 20 °C
With 2,3,3,4,4,5-hexamethyl-2-hexanethiol; water; 1,1'-azobis(1-cyanocyclohexanenitrile); In toluene;
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, room temp., 16 h; 2.) THF, 15 deg C, 3.5 h
2: 10 percent / n-BuLi / tetrahydrofuran / 1.5 h / Ambient temperature
With n-butyllithium; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, room temp., 16 h; 2.) THF, 15 deg C, 3.5 h
2: 42 percent / CH2CHOLi / tetrahydrofuran / 24 h / Heating
With n-butyllithium; Lithium enolate of the acetaldehyde; In tetrahydrofuran;
With sodium tetrahydroborate; In methanol; water; at 20 ℃; for 0.2h; Green chemistry;
> 99 %Chromat.
With sodium tetrahydroborate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; In methanol; water; at 20 ℃; for 0.166667h;
With sodium tetrahydroborate; In water; at 20 ℃; for 0.0666667h; Green chemistry;
> 99 %Chromat.
2-(3-methoxyphenoxy)propanamide
60770-72-1

2-(3-methoxyphenoxy)propanamide

Conditions
Conditions Yield
With potassium hydroxide; In dimethyl sulfoxide; at 140 ℃; for 8h; Green chemistry;
87%
N'-(3-methoxy-phenyl)-N,N-dimethyl-formamidine

N'-(3-methoxy-phenyl)-N,N-dimethyl-formamidine

Conditions
Conditions Yield
With hydrogen; palladium dihydroxide; In water; tert-butyl alcohol; at 20 ℃; for 12h; under 3361.46 Torr;
98%
C<sub>8</sub>H<sub>7</sub>BrCuMgNO

C8H7BrCuMgNO

Conditions
Conditions Yield
C8H7BrCuMgNO; With acetone O-(4-chlorophenylsulfonyl)oxime; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere;
With hydrogenchloride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
71%

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