78317-78-9

Basic information

• Product Name: 2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 78317-78-9
• Molecular Weight: 243.736
• Mol File: 78317-78-9.mol
• Article Data: 37

Chemical Properties

• CAS DataBase Reference: 2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline(78317-78-9)
• EPA Substance Registry System: 2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline(78317-78-9)

Safety Data

• Hazardous Substances Data: 78317-78-9(Hazardous Substances Data)

Upstream product

• 102912-87-8 [1-(2-Bromo-phenyl)-meth-(E)-ylidene]-(4-chloro-phenyl)-amine 
• 106-47-8 4-chloro-aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 356531-18-5 N-(2-bromobenzyl)-4-chloroaniline 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 493-05-0 isochromane 
• 13519-75-0 N-ethyl-4-chloro-aniline 
• 106-39-8 bromochlorobenzene 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 637-87-6 1-Chloro-4-iodobenzene 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 

Downstream Products

• 1477520-57-2 C₂₂H₂₄ClNO₄ 
• 1419612-86-4 2-(4-chlorophenyl)-1-(5-methyl-1H-indol-3-yl)-1,2,3,4-tetrahydroisoquinoline 
• 1419612-82-0 1-(2-chloro-1H-indol-3-yl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1419612-79-5 1-(1H-indol-3-yl)-2-(4-chloro-phenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1454666-99-9 dimethyl (2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phosphonate 
• 1422287-45-3 1-(2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)hexan-2-one 
• 1391634-83-5 (S)-2-(2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acrylaldehyde 
• 1391634-99-3 (S)-3-(2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)but-3-en-2-one 

Relevant articles and documents

Thiyl radical promoted iron-catalyzed-selective oxidation of benzylic sp3 C-H bonds with molecular oxygen

A ligand-free iron-catalyzed method for the oxygenation of benzylic sp3 C-H bonds by molecular oxygen (1 atm) using a thiyl radical as a cocatalyst has been developed. This transformation provides a facile access to amides, esters and ketones from readily accessible corresponding amines, ethers and alkanes. It features high regioselectivity, mild oxidative conditions and excellent functional group compatibility, providing good opportunities to the site-selective functionalization of complex molecules. Preliminary mechanistic studies suggest that this reaction may not undergo a benzylic cation intermediate pathway and the carbonyl oxygen atom in the products may be derived from molecular oxygen.

A Short Approach to N -Aryl-1,2,3,4-tetrahydroisoquinolines from N -(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N -Alkylation Sequence

N -Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho -brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N -aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho -ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N -aryl-1,2,3,4-tetrahydroisoquinolines.

Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines

This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).