Cas no 836-41-9 (1-(4-methoxyphenyl)-N-phenyl-methanimine)

1-(4-Methoxyphenyl)-N-phenylmethanimine is a Schiff base compound characterized by its imine functional group (–C=N–) linking a 4-methoxyphenyl and a phenyl moiety. This structure imparts notable stability and reactivity, making it valuable in organic synthesis, particularly as an intermediate for pharmaceuticals, agrochemicals, and coordination chemistry. The electron-donating methoxy group enhances its utility in nucleophilic reactions and metal complex formation. Its crystalline form ensures ease of handling and purification, while its defined molecular weight (209.25 g/mol) allows precise stoichiometric use. The compound’s compatibility with a range of solvents further broadens its application scope in research and industrial processes.
1-(4-methoxyphenyl)-N-phenyl-methanimine structure
836-41-9 structure
Product Name:1-(4-methoxyphenyl)-N-phenyl-methanimine
CAS No:836-41-9
MF:C14H13NO
MW:211.259123563766
MDL:MFCD00025836
CID:83126
PubChem ID:87572611
Update Time:2025-05-27

1-(4-methoxyphenyl)-N-phenyl-methanimine Chemical and Physical Properties

Names and Identifiers

    • (E)-N-(4-Methoxybenzylidene)aniline
    • p-Anisaldehyde anil~N-(4-Methoxybenzal)aniline
    • N-(4-Methoxybenzylidene)aniline
    • 4'-METHOXYBENZYLIDENEANILINE
    • N-(p-Methoxybenzylidene)aniline
    • N-(p-Anisal)aniline
    • N-(p-Anisylidene)aniline
    • 1-(4-methoxyphenyl)-N-phenyl-methanimine
    • Aniline, N-(p-methoxybenzylidene)- (6CI, 7CI, 8CI)
    • N-[(4-Methoxyphenyl)methylene]benzenamine (ACI)
    • (4-Methoxybenzylidene)aniline
    • (4-Methoxybenzylidene)phenylamine
    • (4-Methoxyphenylmethylene)(phenyl)amine
    • (p-Methoxybenzylidene)aniline
    • N-[(4-Methoxyphenyl)methylene]phenylamine
    • N-Phenyl-4-methoxybenzylideneimine
    • NSC 155535
    • p-Methoxybenzalaniline
    • p-Methoxybenzaldehyde anil
    • 4-Methoxybenzyliden-anilin
    • 836-41-9
    • LS-14280
    • D79200
    • N-(4-Methoxybenzylidene)aniline, 97%
    • M0582
    • Benzenamine, N-[(4-methoxyphenyl)methylene]-
    • FT-0629234
    • NSC-155535
    • F0401-0055
    • DTXSID901303305
    • MFCD00025836
    • (E)-1-(4-methoxyphenyl)-N-phenylmethanimine
    • 1-(4-methoxyphenyl)-N-phenylmethanimine
    • HMS1416L15
    • N-p-Anisylideneaniline
    • BDBM50529593
    • doi:10.14272/MSWPGMRTURVKRJ-RVDMUPIBSA-N
    • 5C-039
    • (1E)-1-(4-methoxyphenyl)-N-phenylmethanimine
    • 10.14272/MSWPGMRTURVKRJ-RVDMUPIBSA-N
    • 4-Methoxybenzylideneaniline
    • p-methoxybenzylidene-phenyl-amine
    • SY049611
    • CS-0183033
    • Anisalanilin
    • EINECS 212-647-8
    • SCHEMBL443412
    • N-[(4-Methoxyphenyl)methylidene]aniline #
    • N-[(4-methoxyphenyl)methylene]benzenamine
    • EU-0034533
    • CHEMBL4475486
    • NS00042982
    • IFLab1_001665
    • AKOS001589886
    • NSC155535
    • 1613-96-3
    • N-(4-Methoxybenzylidene)aniline, >98.0%(GC)(T)
    • MSWPGMRTURVKRJ-RVDMUPIBSA-N
    • Benzenamine, N-[(4-methoxyphenyl)methylene]-, [N(E)]-
    • STL025259
    • Benzenamine, N-((4-methoxyphenyl)methylene)-
    • N-[(E)-(4-Methoxyphenyl)methylidene]aniline
    • DB-056728
    • MDL: MFCD00025836
    • Inchi: 1S/C14H13NO/c1-16-14-9-7-12(8-10-14)11-15-13-5-3-2-4-6-13/h2-11H,1H3
    • InChI Key: MSWPGMRTURVKRJ-UHFFFAOYSA-N
    • SMILES: N(C1C=CC=CC=1)=CC1C=CC(OC)=CC=1
    • BRN: 642337

Computed Properties

  • Exact Mass: 211.10000
  • Monoisotopic Mass: 211.099714038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 213
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 21.6?2

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 61.0 to 67.0 deg-C
  • PSA: 21.59000
  • LogP: 3.44580
  • Solubility: Not determined

1-(4-methoxyphenyl)-N-phenyl-methanimine Security Information

1-(4-methoxyphenyl)-N-phenyl-methanimine Customs Data

  • HS CODE:2925290090
  • Customs Data:

    China Customs Code:

    2925290090

    Overview:

    2925290090 Other imines and their derivatives,And their salt.Regulatory conditions:nothing.VAT:17.0%.Tax refund rate:9.0%.MFN tariff:6.5%.general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2925290090 other imines and their derivatives; salts thereof.Supervision conditions:None.VAT:17.0%.Tax rebate rate:9.0%.MFN tariff:6.5%.General tariff:30.0%

1-(4-methoxyphenyl)-N-phenyl-methanimine Pricemore >>

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1-(4-methoxyphenyl)-N-phenyl-methanimine Production Method

Production Method 1

Reaction Conditions
1.1 Catalysts: Manganese zirconium oxide Solvents: Toluene ;  3 h, 1 atm, 80 °C
Reference
Efficient imine synthesis via oxidative coupling of alcohols with amines in an air atmosphere using a mesoporous manganese-zirconium solid solution catalyst
Wu, Shipeng; et al, Catalysis Science & Technology, 2021, 11(3), 810-822

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Copper ,  Silica Solvents: Toluene ;  0.5 h, 1 atm, 100 °C
Reference
Reductive Amination of Ketones or Amination of Alcohols over Heterogeneous Cu Catalysts: Matching the Catalyst Support with the N-Alkylating Agent
Santoro, Federica; et al, ChemCatChem, 2012, 4(9), 1249-1254

Production Method 3

Reaction Conditions
1.1 2 - 2.1 kPa, 80 °C
Reference
Alkoxy substituted (E,E)-3,6-bis(styryl)pyridazine-a photosensitive mesogen for liquid crystals
Lifka, Thorsten; et al, Tetrahedron, 2008, 64(27), 6551-6560

Production Method 4

Reaction Conditions
1.1 Solvents: Benzene-d6 ;  1 h, 25 °C
Reference
Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
Junor, Glen P. ; et al, Angewandte Chemie, 2019, 58(9), 2875-2878

Production Method 5

Reaction Conditions
1.1 Solvents: Benzene-d6 ;  0.5 h, rt
Reference
Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides
Gudun, Kristina A.; et al, Advanced Synthesis & Catalysis, 2022, 364(3), 601-611

Production Method 6

Reaction Conditions
1.1 Catalysts: Cobalt ,  Carbon nitride (C3N4) Solvents: Ethanol ,  Formic acid ;  12 h, 70 °C
Reference
Cobalt-Doped g-C3N4 Nanosheets for One-Pot Synthesis of Imines under Mild Conditions
Zhu, Jiukang; et al, ACS Applied Nano Materials, 2023, 6(7), 5127-5135

Production Method 7

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Ferrous bromide ;  6 h, 110 °C
Reference
A Solvent-Free Process for Synthesis of Imines by Iron-Catalyzed Oxidative Self- or Cross-Condensation of Primary Amines Using Molecular Oxygen as Sole Oxidant
Gopalaiah, Kovuru; et al, Catalysis Letters, 2016, 146(9), 1648-1654

Production Method 8

Reaction Conditions
1.1 Catalysts: (SP-5-52)-Carbonylhydro[[N,N′-(2,6-pyridinediyl-κN)bis[P,P-bis(1,1-dimethylethyl… ;  160 °C
Reference
Enhanced Reactivities toward Amines by Introducing an Imine Arm to the Pincer Ligand: Direct Coupling of Two Amines To Form an Imine Without Oxidant
He, Li-Peng; et al, Organometallics, 2012, 31(14), 5208-5211

Production Method 9

Reaction Conditions
1.1 Reagents: Indium trichloride Solvents: Acetonitrile
Reference
An indium mediated efficient chemoselective deoxygenation of N-oxides and nitrones
Ilias, Md.; et al, Tetrahedron Letters, 2002, 43(10), 1877-1879

Production Method 10

Reaction Conditions
1.1 Reagents: Cesium hydroxide Catalysts: 1,10-Phenanthroline ,  Cobalt (reaction product with 1,10-phenanthroline/HMTA/Melamine, carbon-suppor…) Solvents: Toluene ;  24 h, 130 °C
Reference
Heterogeneous cobalt-catalyzed degradation of azo compounds using alcohols as the stoichiometric hydrogen source
Panja, Dibyajyoti; et al, Journal of Environmental Chemical Engineering, 2023, 11(2),

Production Method 11

Reaction Conditions
1.1 Solvents: Ethanol ;  3 h, reflux
Reference
Synthesis of structurally diverse 2-azetidinones via Staudinger reaction on a solid support
Jarrahpour, Aliasghar; et al, Bulletin of the Chemical Society of Japan, 2011, 84(3), 320-327

Production Method 12

Reaction Conditions
1.1 Reagents: Triphenylphosphine ,  Potassium hydroxide Catalysts: (OC-6-12)-Dichloro[4-[[(S)-ethylthio-κS]methyl]acridine-κN](triphenylphosphine)r… Solvents: Toluene ;  rt → 135 °C; 18 h, 135 °C
Reference
Acceptorless dehydrogenative construction of C=N and C=C bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex
Biswas, Nandita; et al, Dalton Transactions, 2019, 48(19), 6501-6512

Production Method 13

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: 2633072-21-4 Solvents: Toluene ;  18 h, 130 °C
Reference
Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
Li, Huaifeng; et al, ACS Catalysis, 2021, 11(7), 4071-4076

Production Method 14

Reaction Conditions
1.1 Catalysts: Titanium tetrabutoxide Solvents: Tetrahydrofuran ;  rt; 54 h, rt
1.2 Reagents: Water ;  rt; 1 h, rt
Reference
Room temperature metathesis of aryl isocyanates and aromatic aldehydes catalyzed by group(IV) metal alkoxides: An experimental and computational study
Kumar, Akshai; et al, Journal of Organometallic Chemistry, 2010, 695(3), 338-345

Production Method 15

Reaction Conditions
1.1 Solvents: Ethanol ;  20 min, 50 °C
Reference
(R)-oxynitrilases as biocatalysts for the addition of cyanide to phenylimines
Solis O., Aida; et al, Revista Mexicana de Ciencias Farmaceuticas, 2002, 33(4), 27-31

Production Method 16

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Gold alloy, base, Au 65,Pd 35 (nanoparticles, zirconia-supported) Solvents: Ethanol ;  9 h, 40 °C
1.2 1 h, 40 °C
Reference
Au-Pd alloy nanoparticle catalyzed selective oxidation of benzyl alcohol and tandem synthesis of imines at ambient conditions
Cui, Wenjing ; et al, Catalysis Today, 2014, 235, 152-159

Production Method 17

Reaction Conditions
1.1 Catalysts: Cobalt (composite with carbon and nitrogen; carbon nanotube encapsulated) ;  20 h, 160 °C
Reference
Direct reductive coupling of nitroarenes and alcohols catalysed by Co-N-C/CNT@AC
Liu, Di; et al, Green Chemistry, 2019, 21(8), 2129-2137

Production Method 18

Reaction Conditions
1.1 Catalysts: Cobalt Solvents: Octane ;  12 h, 0.6 MPa, 140 °C
Reference
Preparation of Co-N-C catalysts and "one-pot method" for synthesis of N-benzyl aniline
Leng, Jie; et al, Huagong Xuebao (Chinese Edition), 2020, 71(11), 5016-5024

Production Method 19

Reaction Conditions
1.1 Catalysts: 1-Butanaminium, N,N,N-tributyl-, stereoisomer of diaqua[μ10-[orthosilicato(4-)-κ… Solvents: Acetonitrile ,  Toluene ;  4 h, 60 °C; 2 h, 100 °C
Reference
Visible-Light-Responsive Multielectron Redox Catalysis of Lacunary Polyoxometalates Induced by Substrate Coordination to Their Lacuna
Suzuki, Kosuke; et al, Chemistry - An Asian Journal, 2015, 10(1), 144-148

Production Method 20

Reaction Conditions
1.1 Solvents: Benzene ;  4 h, reflux
Reference
Applications of dynamic combinatorial chemistry for the determination of effective molarity
Ciaccia, Maria; et al, Chemical Science, 2015, 6(1), 144-151

Production Method 21

Reaction Conditions
1.1 Reagents: Pinacolborane Catalysts: Cobalt(II) acetylacetonate ,  Bis[2-(diphenylphosphino)phenyl] ether Solvents: Benzene-d6 ;  1 h, rt
1.2 Solvents: Benzene-d6 ;  0.5 h, rt
Reference
Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides
Gudun, Kristina A.; et al, Advanced Synthesis & Catalysis, 2022, 364(3), 601-611

Production Method 22

Reaction Conditions
1.1 Reagents: Carbon monoxide ,  Water Catalysts: Gold ,  Titania Solvents: Triethylamine ;  1 h, 5 atm, 25 °C
Reference
Direct one-pot reductive imination of nitroarenes using aldehydes and carbon monoxide by titania supported gold nanoparticles at room temperature
Huang, Jun; et al, Green Chemistry, 2011, 13(10), 2672-2677

Production Method 23

Reaction Conditions
1.1 Reagents: tert-Butyl hydroperoxide Catalysts: Chitosan (Cu/chitosan bead complex) Solvents: Acetonitrile ;  24 h, 80 °C
Reference
Uniform Cu/chitosan beads as a green and reusable catalyst for facile synthesis of imines via oxidative coupling reaction
Chutimasakul, Threeraphat; et al, RSC Advances, 2020, 10(35), 21009-21018

Production Method 24

Reaction Conditions
1.1 Reagents: 1,5-Diazabicyclo[4.3.0]non-5-ene Catalysts: Carbon dioxide ,  Eosin Solvents: Dimethyl sulfoxide ;  48 h, 1 atm, 25 - 30 °C
Reference
CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies
Riemer, Daniel; et al, ACS Catalysis, 2018, 8(12), 11679-11687

Production Method 25

Reaction Conditions
1.1 Reagents: Sodium borohydride Catalysts: Chloro(triphenylphosphine)gold ,  3,6,9,12-Tetraoxatridecan-1-ol, 13-(4-ethenylphenyl)-, polymer with ethenylbenze… Solvents: Tetrahydrofuran ,  Diglyme ;  rt; 3 h, rt
1.2 Solvents: Mesitylene ;  5 h, 150 °C
1.3 Reagents: Oxygen Solvents: Toluene ;  20 h, 100 °C
Reference
Aerobic oxidation of amines catalyzed by polymer-incarcerated Au nanoclusters: effect of cluster size and cooperative functional groups in the polymer
Miyamura, Hiroyuki; et al, Bulletin of the Chemical Society of Japan, 2011, 84(6), 588-599

Production Method 26

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Gold ,  Graphite Solvents: Toluene ;  24 h, 110 °C
Reference
Graphite-Supported Gold Nanoparticles as Efficient Catalyst for Aerobic Oxidation of Benzylic Amines to Imines and N-Substituted 1,2,3,4-Tetrahydroisoquinolines to Amides: Synthetic Applications and Mechanistic Study
So, Man-Ho; et al, Chemistry - An Asian Journal, 2009, 4(10), 1551-1561

Production Method 27

Reaction Conditions
1.1 Reagents: Potassium hydroxide ,  Oxygen ;  24 h, 135 °C
Reference
Base-mediated synthesis of imines and amines from N-phenylureas and alcohols
Yadav, Dilip Kumar T.; et al, Synlett, 2014, 25(11), 1611-1615

Production Method 28

Reaction Conditions
1.1 Reagents: Indium ,  Ammonium chloride Solvents: Methanol
Reference
Indium-mediated deoxygenation of nitrones, N-oxides and deoxygenative reductive coupling of nitrones to vicinal diamines
Jeevanandam, Arumugasamy; et al, Synthetic Communications, 2000, 30(17), 3153-3160

Production Method 29

Reaction Conditions
1.1 Reagents: Triphenylphosphine ,  Iodine Solvents: Benzene
Reference
Deoxygenation of α-aryl-N-phenylnitrones with diiodotriphenylphosphorane
Furukawa, Isao; et al, Nippon Kagaku Kaishi, 1989, (10), 1748-52

Production Method 30

Reaction Conditions
1.1 Reagents: Potassium carbonate Catalysts: 2923249-07-2 Solvents: Toluene ;  20 h, 130 °C
Reference
Chemodivergent coupling of azoarenes with benzyl alcohols via a borrowing hydrogen strategy using a well-defined nickel catalyst
Bansal, Sadhna; et al, Catalysis Science & Technology, 2023, 13(9), 2705-2713

Production Method 31

Reaction Conditions
1.1 Reagents: Triphenylphosphine Catalysts: Methyltrioxorhenium Solvents: Benzene ;  10 min, rt
1.2 2 h, rt
Reference
Organic Reactions Catalyzed by Methylrhenium Trioxide: Reactions of Ethyl Diazoacetate and Organic Azides
Zhu, Zuolin; et al, Journal of the American Chemical Society, 1996, 118(41), 9901-9907

Production Method 32

Reaction Conditions
1.1 Catalysts: Potassium hydroxide ;  24 h, 135 °C
Reference
Base-catalyzed synthesis of amides and imines via C-C and C=C bond cleavage
Yadav, Dilip Kumar T.; et al, RSC Advances, 2015, 5(16), 12387-12391

Production Method 33

Reaction Conditions
1.1 Reagents: Boron trifluoride etherate ,  Oxygen Solvents: Acetonitrile-d3
Reference
Oxidative carbon-carbon bond cleavage reaction of 1,2-diamines and 1,2-amino alcohols under an oxygen atmosphere
Shimizu, Makoto; et al, Tetrahedron Letters, 2001, 42(50), 8865-8868

Production Method 34

Reaction Conditions
1.1 Catalysts: Acetic acid
Reference
A simple high yield conversion of imidoyl chlorides to imines and amines
Alper, Howard; et al, Synthesis, 1978, (10), 781-2

Production Method 35

Reaction Conditions
1.1 Solvents: Ethanol ;  overnight, rt
Reference
N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
Ramarao, Jakkula; et al, RSC Advances, 2022, 12(13), 7621-7625

1-(4-methoxyphenyl)-N-phenyl-methanimine Raw materials

1-(4-methoxyphenyl)-N-phenyl-methanimine Preparation Products

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