Benzenamine, N-(phenylmethylene)-, N-oxide

Base Information

• Chemical Name: Benzenamine, N-(phenylmethylene)-, N-oxide
• CAS No.: 1137-96-8
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.236
• European Community (EC) Number: 214-509-2
• NSC Number: 102882
• UNII: L7MP2M8WUP
• Wikidata: Q76149902
• ChEMBL ID: CHEMBL1865314
• Mol file: 1137-96-8.mol

Synonyms:C,N-diphenylnitrone

Chemical Property of Benzenamine, N-(phenylmethylene)-, N-oxide

Chemical Property:

• Vapor Pressure: 7.55E-05mmHg at 25°C
• Melting Point: 113-114°C
• Refractive Index: 1.6050 (estimate)
• Boiling Point: 352.9°Cat760mmHg
• PKA: 0.10±0.53(Predicted)
• Flash Point: 167.6°C
• PSA: 28.75000
• Density: 1.141g/cm³
• LogP: 3.47070
• Water Solubility.: Soluble in water at 25°C, 1120 mg/L.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 197.084063974
• Heavy Atom Count: 15
• Complexity: 213

Purity/Quality:

97% ^*data from raw suppliers

n-phenyl-n-[(z)-phenylmethylidene]amineoxide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=[N+](C2=CC=CC=C2)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)/C=[N+](/C2=CC=CC=C2)\[O-]
• Uses: It is used as a pharmaceutical intermediate.

Technology Process of Benzenamine, N-(phenylmethylene)-, N-oxide

There total 23 articles about Benzenamine, N-(phenylmethylene)-, N-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-benzyl-N-phenylhydroxylamine (3376-40-7) → N-(benzylidene)aniline N-oxide (1137-96-8,26505-49-7,201024-81-9)

Guidance literature:

With rhodium nanoparticles supported on carbon nanotube; In methanol; at 20 ℃; for 2h;

DOI:10.1002/cctc.201601155

Reference yield: 98.0%

benzaldehyde (100-52-7) + N-Phenylhydroxylamine (100-65-2) → N-(benzylidene)aniline N-oxide (1137-96-8,26505-49-7,201024-81-9)

Guidance literature:

In glycerol; at 60 - 80 ℃; for 0.25h; Green chemistry;

DOI:10.1007/s12039-019-1677-7

Reference yield: 94.0%

benzaldehyde (100-52-7) + aniline (62-53-3) → N-(benzylidene)aniline N-oxide (1137-96-8,26505-49-7,201024-81-9)

Guidance literature:

With Oxone; In acetonitrile; at 5 - 20 ℃; for 4.5h; Reagent/catalyst; Solvent; Green chemistry;

DOI:10.1016/j.tetlet.2014.08.049

upstream raw materials:

benzaldehyde

nitrobenzene

N-Phenylhydroxylamine

benzylidene phenylamine

Downstream raw materials:

2,3-Diphenyl-1-oxa-6,10-dithia-2-aza-spiro[4.5]decane

3-acetyl-2-phenylindole

2-phenyl-3,5-dimethyl-4-(phenylsulfonyl)-3-<(phenylsulfonyl)methyl>-Δ⁴-isoxazoline

2,3-diphenyl-5-methyl-4-(phenylsulfonyl)-2,3-dihydroisoxazole

Refernces

High Asymmetric Induction in the 1,3-Dipolar Cycloaddition of (R)-(+)-p-Tolyl Vinyl Sulfoxide with Acyclic Nitrones

10.1021/jo00141a046

The research focuses on the exploration of asymmetric 1,3-dipolar cycloadditions, a field that has been less studied compared to asymmetric Diels-Alder reactions. The purpose of the study was to investigate the high chiral induction potential of a chiral vinyl sulfoxide, (R)-(+)-p-tolyl vinyl sulfoxide, in its reaction with typical acyclic nitrones. The researchers observed high chiral induction in these reactions, which suggests the potential use of this sulfoxide as a chiral inducing agent in cycloadditions. The study concluded with the successful synthesis and characterization of various isoxazolidines and their subsequent transformations, demonstrating the effectiveness of the chiral sulfoxide in inducing asymmetry. Key chemicals used in the process included (R)-(+)-p-tolyl vinyl sulfoxide, C,N-diphenylnitrone, and various reagents for the transformations and analyses, such as LiAlH4 for reduction, CH3-O and NaB3H3CN for N-methylation, and Eu(hfcI3) as a chiral NMR shift reagent for determining enantiomeric excess.