3340-78-1

Basic information

• Product Name: 2-phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 2-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 3340-78-1
• Molecular Formula: C₁₅H₁₅N
• Molecular Weight: 209.2863
• Mol File: 3340-78-1.mol

Chemical Properties

• Melting Point: 45-46 °C
• Boiling Point: 198 °C(Press: 16 Torr)
• Appearance: /
• Density: 1.092±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.94±0.40(Predicted)
• CAS DataBase Reference: 2-phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-1,2,3,4-tetrahydroisoquinoline(3340-78-1)
• EPA Substance Registry System: 2-phenyl-1,2,3,4-tetrahydroisoquinoline(3340-78-1)

Safety Data

• Hazardous Substances Data: 3340-78-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Phenyl-1,2,3,4-tetrahydroisoquinoline is used as a reactant in acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at the α-position of tertiary amines. This application is significant as it allows for the creation of new carbon-carbon bonds without the need for metal catalysts, which can be advantageous in terms of cost, environmental impact, and reaction conditions.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, due to its structural similarity to various bioactive compounds, could potentially be used in the pharmaceutical industry as a starting material or intermediate for the synthesis of drugs targeting specific receptors or enzymes. Its reactivity and structural features make it a promising candidate for the development of novel therapeutic agents.

Upstream product

• 493-05-0 isochromane 
• 62-53-3 aniline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 3076-54-8 phenyllead(IV) triacetate 
• 603-33-8 triphenylbismuthane 
• 38256-56-3 1-(2-bromo-ethyl)-2-bromomethyl-benzene 
• 325723-04-4 Phenylbiphenyl-2,2'-ylenebismuth diacetate 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 78317-75-6 1-(2-chloroethyl)-2-chloromethylbenzene 
• 102-96-5 (2-nitroethenyl)benzene 
• 100-52-7 benzaldehyde 
• 64-04-0 phenethylamine 

Downstream Products

• 55662-89-0 2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 

Relevant articles and documents

The Photocatalyzed Aza-Henry Reaction of N-Aryltetrahydroisoquinolines: Comprehensive Mechanism, H?- versus H+-Abstraction, and Background Reactions

The cross-dehydrogenative coupling (CDC) reaction of N-aryltetrahydroisoquinolines (THIQ) is one of the most exploited photocatalytic transformation and a test reaction for an exceptional variety of catalysts. However, its mechanism remained unclear conce

CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds

A novel and efficient C-C bond formation method was developed via the cross-dehydrogenative coupling (CDC) reaction of indoles and tetrahydroisoquinolines catalyzed by copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct indolyl tetrahydroisoquinolines via a combination of sp3 C-H bond and sp2 C-H bond followed by C-C bond formation. Copyright

Direct Near Infrared Light–Activatable Phthalocyanine Catalysts

The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa

Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis

A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.

Effect of Precatalyst Oxidation State in C-N Cross-Couplings with 2-Phosphinoimidazole-Derived Bimetallic Pd(I) and Pd(II) Complexes

We report the catalytic activity of two phosphinoimidazole-derived bimetallic palladium complexes in Pd-catalyzed amination reactions. Our studies demonstrate that the starting oxidation state (Pd(I) or Pd(II)) of the dimeric complex has a significant effect on the efficiency of the catalytic reaction. The corresponding Pd(I) complex shows higher reactivity in Buchwald-Hartwig aminations, while the Pd(II) complex is much more reactive in carbonylative amination reactions. These new dimeric palladium complexes provide good to excellent reactivity and yields in the amination reactions tested.

Electrocatalytic C(sp3)-H/C(sp)-H cross-coupling in continuous flow through TEMPO/copper relay catalysis

Electrocatalytic dehydrogenative C(sp3)-H/C(sp)-H cross-coupling of tetrahydroisoquinolines with terminal alkynes has been achieved in a continuous-flow microreactor through 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)/copper relay catalysis. The reaction

Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones

Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.

Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide: A New Synthetic Approach to α-Monofluoromethyl Tertiary Amines

A cross dehydrogenative coupling reaction of tetrahydroisoquinolines with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide had been developed. CuBr/TBHP was identified as the best catalyst and oxidant. A variety of coupling products were obtained with good t

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-Tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

An oxidant- And catalyst-free electrooxidative cross-coupling approach to 3-tetrahydroisoquinoline substituted coumarins

A direct electrooxidative cross-dehydrogenative-coupling (CDC) reaction betweenN-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins has been realized. This protocol provides a green, mild and fast method to construct 3-tetrahydroisoquinoline substituted coumarins in the absence of any catalysts and exogenous oxidants. A variety ofN-aryl-tetrahydroisoquinolines and 4-hydroxycoumarins are compatible with this transformation to give the corresponding products in moderate to excellent yields. Moreover, the results of control experiments, cyclic voltammetry experiments, and density functional theory (DFT) calculations indicated that the electrooxidative CDC reaction might involve both radical addition and nucleophilic addition processes.