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Cas Database

15286-52-9

15286-52-9

Identification

  • Product Name:Benzenamine,4-methoxy-N-(3-phenyl-2-propen-1-ylidene)-

  • CAS Number: 15286-52-9

  • EINECS:

  • Molecular Weight:237.301

  • Molecular Formula: C16H15NO

  • HS Code:

  • Mol File:15286-52-9.mol

Synonyms:Benzenamine,4-methoxy-N-(3-phenyl-2-propenylidene)- (9CI); p-Anisidine, N-cinnamylidene-(8CI); N-(3-Phenyl-2-propenylidene)-4-methoxyphenylamine;N-(4-Methoxyphenyl)-3-phenylpropenaldimine; N-Cinnamylidene-p-methoxyaniline;NSC 155533; p-Methoxy-N-cinnamylideneaniline

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Safety information and MSDS view more

  • Signal Word:No signal word.

  • Hazard Statement:H413 May cause long lasting harmful effects to aquatic life

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • 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

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Relevant articles and documentsAll total 26 Articles be found

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Wu, Jiajun,Darcel, Christophe

, p. 1023 - 1036 (2021/01/09)

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Synthesis of β-Phosphinolactams from Phosphenes and Imines

Fu, Xingyang,Li, Xinyao,Xu, Jiaxi

supporting information, p. 8733 - 8737 (2021/11/17)

Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.

Synthesis, characterization, molecular structure and computational study of tetrahedral pentamethylcyclopentadienyl iridacycle complexes with α,β-conjugated Schiff base ligands

Daud, Adibah Izzati,Khairul, Wan M.,Liu, Zhi-Qiang,Ong, Kok Tong,Tay, Meng Guan

, (2020/09/16)

Due to the excellent catalytic activities and phosphorescent properties that iridium complexes display, iridium chemistry has been of great interest for scientific investigation over the past 30 years. Iridium metallacycle analogues (also known as an iridacycles) bearing phenylpyridine (ppy) ligands have been well reported on, whilst complexes with R-phenyl-(3-R-phenylallylidene)amine, which is an α,β-conjugated Schiff base ligand, have not had the same attention, despite the fact that both ligands share a similar coordination mode. In this research, four pentamethylcyclopentadienyl iridacycle complexes, Ir1a-Ir1d, with different α,β-conjugated Schiff base ligands were synthesized from a di-μ-chloro-dichloro-bis-(η5-pentamethylcyclopentadienyl)diiridium(III) precursor. The iridacycle complexes were characterized using spectroscopic techniques and the molecular structures of Ir1ab-Ir1d were determined using X-ray crystallography. The X-ray results revealed that the iridacycle complexes have a tetrahedral geometry, the iridium centre being coordinated through the N[dbnd]C[sbnd]Cα[dbnd]Cβ moiety of the α,β-conjugated Schiff base ligand. Computational calculations with the B3LYP method and with LanL2DZ basis sets indicated that the HOMO-LUMO energy gaps Ir1b-Ir1d were in the range 3.31–3.36 eV. The OMe substituent at the C terminal has a greater impact on the HOMO energy level than the one at the N terminal.

Stereoselective Construction of γ-Lactams via Copper-Catalyzed Borylacylation

Bajohr, Jonathan,Lautens, Mark,Polishchuk, Iuliia,Torelli, Alexa,Whyte, Andrew

supporting information, p. 7915 - 7919 (2020/11/02)

A versatile and highly stereoselective borylative cyclization to generate polyfunctionalized γ-lactams has been developed. The stereoselective synthesis of these key ring systems is crucial due to their ubiquity in natural products. We report the diastero- and enantioselective construction of di- and trisubstituted γ-lactam cores, with examples containing an enantioenriched quaternary carbon.

Promoting Frustrated Lewis Pairs for Heterogeneous Chemoselective Hydrogenation via the Tailored Pore Environment within Metal–Organic Frameworks

Niu, Zheng,Zhang, Weijie,Lan, Pui Ching,Aguila, Briana,Ma, Shengqian

supporting information, p. 7420 - 7424 (2019/04/27)

Frustrated Lewis pairs (FLPs) have recently been advanced as efficient metal-free catalysts for catalytic hydrogenation, but their performance in chemoselective hydrogenation, particularly in heterogeneous systems, has not yet been achieved. Herein, we demonstrate that, via tailoring the pore environment within metal–organic frameworks (MOFs), FLPs not only can be stabilized but also can develop interesting performance in the chemoselective hydrogenation of α,β-unsaturated organic compounds, which cannot be achieved with FLPs in a homogeneous system. Using hydrogen gas under moderate pressure, the FLP anchored within a MOF that features open metal sites and hydroxy groups on the pore walls can serve as a highly efficient heterogeneous catalyst to selectively reduce the imine bond in α,β-unsaturated imine substrates to afford unsaturated amine compounds.

Process route upstream and downstream products

Process route

4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
piperidine; In ethanol; for 5h; Heating;
100%
With magnesium sulfate; In dichloromethane; at 20 ℃;
100%
In ethyl 2-hydroxypropionate; water; at 20 ℃; for 0.025h;
96%
In ethanol;
90%
With magnesium sulfate; In dichloromethane; at 20 ℃; for 6h; Schlenk technique; Inert atmosphere;
80%
In ethanol; Heating;
62%
In dichloromethane; Inert atmosphere; Molecular sieve;
59%
With ethanol;
In ethanol; for 1h; Heating;
In ethanol; Reflux;
With MgI2 etherate [(MgI2.OEt2)n]; In dichloromethane; at 20 ℃; for 0.166667h;
With sodium sulfate; In dichloromethane; at 20 ℃; for 24h;
With magnesium sulfate; at 20 ℃; Inert atmosphere;
In toluene; at 100 ℃; for 1h; Molecular sieve; Inert atmosphere;
In methanol; at 60 ℃; for 3h;
With magnesium sulfate; In dichloromethane; at 20 ℃;
With Amberlyst; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;
With magnesium sulfate; In dichloromethane; at 20 ℃;
p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
With poly(styrene-co-3-maleimidophenyldiphenylphosphine); In tetrahydrofuran; at 20 ℃; for 43h;
97%
N-cinnamyl-4-methoxybenzenamine
22774-93-2

N-cinnamyl-4-methoxybenzenamine

Conditions
Conditions Yield
With tert.-butylhydroperoxide; tris(triphenylphosphine)ruthenium(II) chloride; In benzene; Ambient temperature;
80%
para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
Conditions Yield
With potassium phosphate monohydrate; trimethylamine-N-oxide; C18H27FeO4Si2; In toluene; at 140 ℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;
58%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

4-methoxy-aniline
104-94-9

4-methoxy-aniline

Conditions
Conditions Yield
With magnesium sulfate; In benzene; at 20 ℃;
benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: toluene / 17 h / 85 °C
2: magnesium sulfate / dichloromethane / 20 °C
With magnesium sulfate; In dichloromethane; toluene; 1: |Wittig Olefination;
phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: palladium diacetate; 2.9-dimethyl-1,10-phenanthroline; p-benzoquinone / N,N-dimethyl-formamide / 48.5 h / 20 °C
2: magnesium sulfate / dichloromethane / 20 °C
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; magnesium sulfate; p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; 1: |Heck Reaction;
Conditions
Conditions Yield
96%
entspr. Aldehyd, entspr. Amin;
Benzaldehyd, Phosphoniumsalz 9b;
Zimtaldehyd, p-Anisidin;
entspr. Allylamin, MnO2;
p-Anisidin, N-Cinnamyliden-4-nitro-anilin, beide in abs. Me., Siedetemp., 30 Std.;
4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
piperidine; In ethanol; for 5h; Heating;
100%
With magnesium sulfate; In dichloromethane; at 20 ℃;
100%
In ethyl 2-hydroxypropionate; water; at 20 ℃; for 0.025h;
96%
In ethanol;
90%
With magnesium sulfate; In dichloromethane; at 20 ℃; for 6h; Schlenk technique; Inert atmosphere;
80%
In ethanol; Heating;
62%
In dichloromethane; Inert atmosphere; Molecular sieve;
59%
With ethanol;
In ethanol; for 1h; Heating;
In ethanol; Reflux;
With MgI2 etherate [(MgI2.OEt2)n]; In dichloromethane; at 20 ℃; for 0.166667h;
With sodium sulfate; In dichloromethane; at 20 ℃; for 24h;
With magnesium sulfate; at 20 ℃; Inert atmosphere;
In toluene; at 100 ℃; for 1h; Molecular sieve; Inert atmosphere;
In methanol; at 60 ℃; for 3h;
With magnesium sulfate; In dichloromethane; at 20 ℃;
With Amberlyst; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;
With magnesium sulfate; In dichloromethane; at 20 ℃;
p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
With poly(styrene-co-3-maleimidophenyldiphenylphosphine); In tetrahydrofuran; at 20 ℃; for 43h;
97%

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  • Career Henan Chemical Co
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-371-86658258
  • Emails:purchase@coreychem.com
  • Main Products:137
  • Country:China (Mainland)
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