36556-06-6

Basic information

• Product Name: 5,6,7,8-TETRAHYDROISOQUINOLINE
• Synonyms: 3,4-CYCLOHEXENOPYRIDINE;5,6,7,8-TETRAHYDROISOQUINOLINE;5,6,7,8-TETRAHYDROISOQUINOLINE 98+%;Isoquinoline,5,6,7,8-tetrahydro-;5,6,7,8-Tetrahydroisoquinoline 95%
• CAS NO: 36556-06-6
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• EINECS: 253-098-4
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Isoquinolines
• Mol File: 36556-06-6.mol

Chemical Properties

• Melting Point: 146.5°C
• Boiling Point: 106-108 °C13 mm Hg(lit.)
• Flash Point: 212 °F
• Appearance: Clear pale yellow/Liquid
• Density: 1.03 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.172mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.37±0.20(Predicted)
• CAS DataBase Reference: 5,6,7,8-TETRAHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-TETRAHYDROISOQUINOLINE(36556-06-6)
• EPA Substance Registry System: 5,6,7,8-TETRAHYDROISOQUINOLINE(36556-06-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 36556-06-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5,6,7,8-Tetrahydroisoquinoline is used as a key intermediate in the total synthesis of (±)-desoxycodeine-D, a compound with potential pharmaceutical applications. Its role in this synthesis highlights its importance in the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, 5,6,7,8-tetrahydroisoquinoline is utilized in the synthesis of 7,8-dihydroisoquinolin-5(6H)-one, a compound that may have various applications in chemical research and development. This demonstrates the versatility of 5,6,7,8-tetrahydroisoquinoline as a building block for creating diverse organic molecules.
Used in Research and Development:
5,6,7,8-Tetrahydroisoquinoline is also employed in research and development for its potential applications in creating new compounds and materials. Its unique structure and reactivity make it a valuable tool for chemists and researchers working on the design and synthesis of novel molecules with specific properties and functions.

Synthesis Reference(s)

Tetrahedron, 39, p. 2869, 1983 DOI: 10.1016/S0040-4020(01)92154-4

InChI:InChI=1/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h5-7H,1-4H2

Upstream product

• 38969-63-0 1,3-dichloro-5,6,7,8-tetrahydro-isoquinoline 
• 2744-08-3 (4aS^*,8aS^*)-1,2,3,4,4a,5,6,7,8,8a-perhydroisoquinoline 
• 119-65-3 isoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 21917-88-4 6, 7-dihydro-5H-isoquinolin-8-one 
• 875249-44-8 5,6,7,8-tetrahydro-isoquinoline-3-carboxylic acid-(2-propionyl-anilide) 
• 63177-18-4 2-carboxy-1-cyclohexeneacetic acid 
• 858194-24-8 1-ethoxy-5,6,7,8-tetrahydro-[4]isoquinolylamine 
• 59050-59-8 4-bromo-1-ethoxy-isoquinoline 
• 59050-62-3 1-ethoxy-[4]isoquinolylamine 
• 855651-19-3 1-ethoxy-5,6,7,8-tetrahydro-isoquinoline 
• 36556-02-2 5,6,7,8-tetrahydro-isoquinoline-1,3-diol 
• 3749-21-1 4-bromoisoquinoline N-oxide 
• 66728-98-1 4-bromo-1-chloroisoqionoline 

Downstream Products

• 106203-71-8 1-benzamido-5,6,7,8-tetrahydroisoquinoline 
• 2744-08-3 decahydroisoquinoline 
• 21917-86-2 7,8-dihydroisoquinolin-5(6H)-one 
• 135311-97-6 5,6,7,8-tetrahydroisoquinolin-8-one hydrochloride 
• 21917-88-4 6, 7-dihydro-5H-isoquinolin-8-one 
• 38969-64-1 1-(4-methoxy-benzyl)-2-methyl-1,2,5,6,7,8-hexahydro-isoquinoline 
• 150492-72-1 2-phenethyl-1,2,3,4,5,6,7,8-octahydroisoquinoline 

Relevant articles and documents

Scalable Wolff-Kishner Reductions in Extreme Process Windows Using a Silicon Carbide Flow Reactor

A safe and scalable continuous flow strategy for Wolff-Kishner reductions that employs methanol as the solvent has been developed. The use of low-cost hydrazine as the reducing agent in combination with a caustic base provides an atom-efficient, environmentally friendly method for the deoxygenation of aldehydes and ketones to alkanes. Because of the required harsh and corrosive reaction conditions (200 °C, 50 bar), reactor materials such as stainless steel, glass, or any type of polymer have compatibility problems, rendering this process problematic on a production scale. The use of corrosion-resistant silicon carbide (SiC) as the reactor material opens up the possibility of performing Wolff-Kishner reductions on scale with a considerably improved safety profile. Methanol as the solvent significantly simplifies the workup procedure compared with the generally employed high-boiling solvents such as diethylene glycol. The continuous flow protocol was applied to a number of substrates and provided the desired products in good to high yields with space-time yields of up to 152 g L-1 h-1. In addition, a pharmaceutically valuable active pharmaceutical ingredient precursor was synthesized by employing this higherature/pressure Wolff-Kishner protocol.

Ru-Catalyzed Transfer Hydrogenation of Nitriles, Aromatics, Olefins, Alkynes and Esters

This paper reports the preparation of new ruthenium(II) complexes supported by a pyrazole-phosphine ligand and their application to transfer hydrogenation of various substrates. These Ru complexes were found to be efficient catalysts for the reduction of nitriles and olefins. Heterocyclic compounds undergo transfer hydrogenation with good to moderate yields, affording examples of unusual hydrogenation of all-carbon-rings. Internal alkynes with bulky substituents show selective reduction to olefins with the unusual E–selectivity. Esters with strong electron-withdrawing groups can be reduced to the corresponding alcohols, if ethanol is used as the solvent. Possible mechanisms of hydrogenation and olefin isomerization are suggested on the basis of kinetic studies and labelling experiments.

Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids

N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1-3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs). Particularly a diol-functionalised IL shows the best performance in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline (1THQ) with up to 99% selectivity.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF RESPIRATORY DISORDERS

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of respiratory disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of cough caused by minor throat and bronchial irritation (such as commonly accompanies the flu and common cold), as well as those resulting from inhaled particle irritants, upper respiratory infections, (pseudobulbar affect) in patients with amyotrophic lateral sclerosis and multiple sclerosis, neuropathic pain and pain associated with fibromyalgia.

SUBSTITUTED BICYCLIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted bicyclic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.

Substituted Bicyclic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands

Substituted bicyclic carboxamide and urea compounds corresponding to formula (I) processes for the preparation thereof, pharmaceutical compositions containing these compounds, and a method of using these compounds for the treatment and/or inhibition of pain and other conditions mediated at least in part via the vanilloid receptor 1.

Superacidic activation of quinoline and isoquinoline; their reactions with cyclohexane and benzene

(Chemical Equation Presented) Quinoline (1) and isoquinoline (2), upon activation by strong acids, lead to intermediate N,C-diprotonated dications, which are involved in reactions with weak nucleophiles. Thus, 1 and 2 undergo selective ionic hydrogenation with cyclohexane in CF3SO 3H-SbF5, HBr-AlBr3-CH2Br 2, or HCl-AlCl3-CH2Cl2 acid systems to give their 5,6,7,8-tetrahydro derivatives. They also readily condense with benzene in the presence of HBr-AlBr3 or HCl-AlCl3 to provide 5,6,7,8-tetrahydro-5,7-diphenylquinoline (10) and 5,6,7,8-tetrahydro-6, 8-diphenylisoquinoline (12), respectively.

Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids

Isomeric 5-, 6-, 7-hydroxyquinolines (11-13) and 5-hydroxyisoquinoline (14) gave N,C-diprotonated dications in CF3SO3H-SbF5 superacid medium. Compounds 11, 13, 14, and 8-hydroxyquinoline (5) underwent selective ionic hydro

Substituted 2-[monoannelated (3,4-,4,5-, and 5,6-) pyridylalkylenesulfinyl]benzimidazoles

The present invention provides novel substituted 2-[monoannelated(3,4- 4,5-, and 5,6-)pyridylalkylenesulfinyl]-benzimidazoles with gastric acid inhibiting effects.

Mechanism of Isomerization of 1,2,3,4-Tetrahydroisoquinoline to 5,6,7,8-Tetrahydroisoquinoline over Raney Nickel

The isomerization of 1,2,3,4-tetrahydroisoquinoline to 5,6,7,8-tetrahydroisoquinoline proceeded over Raney nickel at ca. 200 deg C under hydrogen and nitrogen pressure in a closed reactor.Based on kinetic analyses and quantum chemical calculations we propose that the isomerization proceeds through a series of consecutive steps where dehydrogenation and hydrogenation take place in an alternate manner.The isomerization is initiated by dehydrogenation at the C-1 and N positions of 1,2,3,4-tetrahydroisoquinoline to form 3,4-dihydroisoquinoline which, in turn, is rehydrogenated into 3,4,6,7-tetrahydroisoquinoline and 3,4,5,6,7,8-hexahydroisoquinoline.The hexahydroisoquinoline is finally dehydrogenated into the isomerized product.No extra hydrogen appears to be required for the isomerization.Under a nitrogen stream in an open reactor, the selective formation of isoquinoline occurred.