55489-38-8

Basic information

• Product Name: 4-[METHYL(PHENYL)AMINO]BENZALDEHYDE
• Synonyms: 4-[METHYL(PHENYL)AMINO]BENZALDEHYDE;MFCD09040338
• CAS NO: 55489-38-8
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.27
• Mol File: 55489-38-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 369.6°C at 760 mmHg
• Flash Point: 147°C
• Appearance: /
• Density: 1.137g/cm³
• Vapor Pressure: 1.18E-05mmHg at 25°C
• Refractive Index: 1.642
• PKA: -2.33±0.32(Predicted)
• CAS DataBase Reference: 4-[METHYL(PHENYL)AMINO]BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[METHYL(PHENYL)AMINO]BENZALDEHYDE(55489-38-8)
• EPA Substance Registry System: 4-[METHYL(PHENYL)AMINO]BENZALDEHYDE(55489-38-8)

Safety Data

• Hazardous Substances Data: 55489-38-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13NO/c1-15(13-5-3-2-4-6-13)14-9-7-12(11-16)8-10-14/h2-11H,1H3

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 100-61-8 N-methylaniline 
• 104-88-1 4-chlorobenzaldehyde 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 552-82-9 benzhydrylidene(methyl)amine 
• 68-12-2 N,N-dimethyl-formamide 
• 122-39-4 diphenylamine 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant articles and documents

Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines

Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.

Optimization of N-Substituted Oseltamivir Derivatives as Potent Inhibitors of Group-1 and -2 Influenza A Neuraminidases, Including a Drug-Resistant Variant

On the basis of our earlier discovery of N1-selective inhibitors, the 150-cavity of influenza virus neuraminidases (NAs) could be further exploited to yield more potent oseltamivir derivatives. Among the synthesized compounds, 15b and 15c were exceptionally active against both group-1 and -2 NAs. Especially for 09N1, N2, N6, and N9 subtypes, they showed 6.80-12.47 and 1.20-3.94 times greater activity than oseltamivir carboxylate (OSC). They also showed greater inhibitory activity than OSC toward H274Y and E119V variant. In cellular assays, they exhibited greater potency than OSC toward H5N1, H5N2, H5N6, and H5N8 viruses. 15b demonstrated high metabolic stability, low cytotoxicity in vitro, and low acute toxicity in mice. Computational modeling and molecular dynamics studies provided insights into the role of R group of 15b in improving potency toward group-1 and -2 NAs. We believe the successful exploitation of the 150-cavity of NAs represents an important breakthrough in the development of more potent anti-influenza agents.

Direct arylation of tertiary amines via aryne intermediates using diaryliodonium salts

With a strategy by using diaryliodonium salts as the precursors of benzynes, direct N-arylation of tertiary amines with diaryliodonium salts was reported. Thus, the desired aromatic tertiary amines with a wide range of substituents were synthesized in moderate to excellent yields of 55–91%.