5697-85-8

Basic information

• Product Name: o-Phenethylaniline
• Synonyms: o-Phenethylaniline;2-(2-phenylethyl)aniline
• CAS NO: 5697-85-8
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.2756
• Mol File: 5697-85-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 33°C
• Boiling Point: 324.39°C (rough estimate)
• Flash Point: 154.1°C
• Appearance: /
• Density: 1.0430
• Vapor Pressure: 0.000319mmHg at 25°C
• Refractive Index: 1.6095 (estimate)
• PKA: 4.24±0.10(Predicted)
• CAS DataBase Reference: o-Phenethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: o-Phenethylaniline(5697-85-8)
• EPA Substance Registry System: o-Phenethylaniline(5697-85-8)

Safety Data

• Hazardous Substances Data: 5697-85-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H15N/c15-14-9-5-4-8-13(14)11-10-12-6-2-1-3-7-12/h1-9H,10-11,15H2

Upstream product

• 62723-78-8 2-methoxymethylaniline 
• 1589-82-8 phenylmagnesium bromide 
• 26216-91-1 2-phenyl-2,3-dihydro-1H-indole 
• 4714-25-4 2-nitrostilbene 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 4914-12-9 diethyl 2-nitrobenzylphosphonate 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 552-89-6 2-nitro-benzaldehyde 
• 681461-50-7 N-(2-phenethylphenyl)benzamide 
• 4264-29-3 (E)-2-nitrostilbene 
• 52208-62-5 (Z)-2-nitrostilbene 
• 100-42-5 styrene 
• 615-36-1 2-bromoaniline 
• 100-39-0 benzyl bromide 

Downstream Products

• 7294-84-0 2-(2-phenylethyl)phenol 
• 776-35-2 9,10-dihydrophenanthrene 
• 35444-96-3 1-(2-iodophenyl)-2-phenylethane 
• 1259938-74-3 C₂₂H₁₆N₂O₄ 
• 1259938-75-4 C₂₂H₁₆N₂O₄ 
• 1174988-05-6 (E)-N-[3-chloro-1-ethylpyridin-4(1H)-ylidene]-2-phenethylaniline trifluoromethanesulfonate 
• 1186335-53-4 4,5,6,7-tetrachloro-N-[2'-(2-phenylethyl)phenyl]phthalimide 
• 84-11-7 9,10-phenanthrenequinone 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 26216-91-1 2-phenyl-2,3-dihydro-1H-indole 
• 948-65-2 2-phenyl-indole 

Relevant articles and documents

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"bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air

To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture-and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.

Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists

Liver X receptor (LXR) agonists are candidates for the treatment of atherosclerosis via induction of ABCA1 (ATP-binding cassette A1) gene expression, which contributes to reverse cholesterol transport (RCT) and to cholesterol efflux from the liver and intestine. However, LXR agonists also induce genes involved in lipogenesis, such as SREBP-1c (sterol regulatory binding element protein 1c) and FAS (fatty acid synthase), thereby causing an undesirable increase in plasma and hepatic triglyceride (TG) levels. Recent studies indicate that LXRα contributes to lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand-binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue as an LXRβ-selective agonist. Structural development led to (E)-4,5,6,7-tetrachloro-2-(2-styrylphenyl)isoindoline-1,3-dione (24 a), which shows potent and selective LXRβ agonistic activity in reporter gene assays. In binding assays, compound 24 a bound to LXRβ preferentially over LXRα. It also induced the expression of ABCA1 mRNA but not SREBP-1c mRNA in cells. Compound 24 a appears to be a promising lead compound for therapeutic agents to treat atherosclerosis without the side effects induced by LXRα/β dual agonists.