93733-03-0

Basic information

• Product Name: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-nitrophenyl)-
• CAS NO: 93733-03-0
• Molecular Formula: C15H14N2O2
• Molecular Weight: 254.288
• Mol File: 93733-03-0.mol

Chemical Properties

• CAS DataBase Reference: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-nitrophenyl)-(93733-03-0)
• EPA Substance Registry System: Isoquinoline, 1,2,3,4-tetrahydro-2-(4-nitrophenyl)-(93733-03-0)

Safety Data

• Hazardous Substances Data: 93733-03-0(Hazardous Substances Data)

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 100-00-5 4-chlorobenzonitrile 
• 493-05-0 isochromane 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 
• 100-01-6 4-nitro-aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 24067-17-2 4-nitrophenylboronic acid 
• 905718-45-8 [(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate] 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 127827-48-9 2-(4-nitrophenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 1132765-76-4 1-(nitromethyl)-2-(4′-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 41852-30-6 2-(4-nitrophenyl)-3,4-dihydroisoquinolin-2-ium bromide 
• 140381-75-5 N-(4-nitrophenyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 16567-33-2 1-tert-Butylperoxy-2-(4-nitro-phenyl)-1,2,3,4-tetrahydro-isochinolin 
• 94066-12-3 2-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 87993-01-9 diethyl (2-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phosphonate 

Relevant articles and documents

Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions

Due to the particularity of the thiocarbonyl group (C S bond), only limited C(sp3)-H thiocarbonylation methods, especially efficient and convenient methods, have been developed for the synthesis of thioamides. Inspired by the “solvent-specifici

Investigating the Oxidation Step in the CuCl2-Catalyzed Aerobic Oxidative Coupling Reaction of N-Aryl Tetrahydroisoquinolines

The oxidative coupling of N-aryl tetrahydroisoquinolines with nucleophiles has inspired the development of novel C-H functionalization reactions as well as mechanistic studies. Here, we investigate the oxidation step that forms iminium ions as key intermediates in the method using CuCl2 as the catalyst and oxygen as the terminal oxidant. A strong electronic effect of substituents in the N-aryl ring was found by synthetic studies and a Hammett plot analysis, supporting initial electron transfer from the amine to Cu(II). The importance of the mechanism of oxidation on the substrate scope with differently substituted tetrahydroisoquinolines is discussed.

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.

Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions

A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.

Synthesis of Dihydroindoloisoquinolines through Copper-Catalyzed Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes

Lately, the cross-dehydrogenative coupling of tetrahydroisoquinolines and nitroalkanes has become a widely studied reaction in organic chemistry; the corresponding β-nitroamines are generally formed irrespective of the catalysis and activation mode utiliz

N-Aryl Groups Are Ubiquitous in Cross-Dehydrogenative Couplings Because They Stabilize Reactive Intermediates

The mechanism of cross-dehydrogenative coupling (CDC) reactions has been examined by experimental and computational methods. We provide a rationale for the ubiquity of the N-aryl group in these reactions. The aryl substituent stabilizes two intermediates

Copper-Catalyzed Cyanomethylation of Substituted Tetrahydroisoquinolines with Acetonitrile

A novel method for the synthesis of cyanomethylated tetrahydroisoquinolines has been developed with mild reaction conditions, good yields and a broad substrate scope. Acetonitrile, a common solvent, is for the first time used as a pronucleophile for this type of two sp3C?H bonds cross-dehydrogenative coupling (CDC) reaction. A new oxidative system (CuCl2/TEMPO/Cs2CO3) has been established by our group, in which the mild TEMPO reagent was found to be a highly efficient oxidant. (Figure presented.).

Rapid Microwave-Assisted Synthesis of N-Aryl 1,2,3,4-Tetrahydroisoquinolines

N-aryl 1,2,3,4-tetrahydroisoquinolines were prepared rapidly in good yields by the microwave-assisted Pd-catalysed coupling of (hetero)aryl iodides or bromides with 1,2,3,4-tetrahydroisoquinoline. Reactions were typically complete within 5 min for aryl iodides and within 30 min for pyridyl bromides.

Visible-light-induced direct α-C(sp3)-H thiocyanation of tertiary amines

Visible-light-induced, eosin Y catalyzed aerobic oxidative α-C(sp3)-H thiocyanation of tertiary amines is reported. The reaction proceeds through visible-light-induced in situ generation of the iminium ion followed by attack of -SCN nucleophile. This is the first example of visible-light-initiated formation of C(sp3)-S bond employing organo-photoredox catalysis. Mild reaction conditions and use of air and visible light as the greenest and sustainable reagents at room temperature are the salient features of the protocol.

Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines

The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.