6552-60-9

Basic information

• Product Name: 1,2,3,4-TETRAHYDROISOQUINOLINE-1-THIONE
• Synonyms: 1,2,3,4-TETRAHYDROISOQUINOLINE-1-THIONE
• CAS NO: 6552-60-9
• Molecular Formula: C₉H₉NS
• Molecular Weight: 163.24
• Mol File: 6552-60-9.mol

Chemical Properties

• Boiling Point: 278.2°C at 760 mmHg
• Flash Point: 122.1°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0.00431mmHg at 25°C
• Refractive Index: 1.663
• CAS DataBase Reference: 1,2,3,4-TETRAHYDROISOQUINOLINE-1-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAHYDROISOQUINOLINE-1-THIONE(6552-60-9)
• EPA Substance Registry System: 1,2,3,4-TETRAHYDROISOQUINOLINE-1-THIONE(6552-60-9)

Safety Data

• Hazardous Substances Data: 6552-60-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H9NS/c11-9-8-4-2-1-3-7(8)5-6-10-9/h1-4H,5-6H2,(H,10,11)

Upstream product

• 491-30-5 1-isoquinolone 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 2257-09-2 Phenethyl isothiocyanate 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 88252-59-9 1-(3-nitrophenyl)-3,4-dihydroisoquinoline 
• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 104628-87-7 methyl 6,7-dihydro-4-oxo-3-phenyl-4H-benzoquinolizine-1-carboxylate 
• 66491-03-0 7-amino-3,4-dihydroisoquinoline-1(2H)-one 
• 66491-04-1 7-iodo-3,4-dihydro-1(1H)-isoquinolinone 
• 62541-62-2 2-(2-Aminoethyl)-5-iodobenzoic acid hydrochloride 
• 62541-66-6 2-(2-Aminoethyl)-5-nitrobenzoic acid 
• 62541-67-7 2-(2-Pyrrol-1-ylethyl)-5-nitro benzoic acid 
• 62541-63-3 5-Iodo-2-(2-pyrrol-1-ylethyl)benzoic acid 
• 22245-96-1 7-nitro-3,4-dihydro-2H-isoquinolin-1-one 
• 78874-09-6 2-<(3,4-Dihydro-1-isoquinol-1-yl)thio>cyclohexanone 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 104728-22-5 5,6-dihydro-2-phenylthiazolo<2,3-a>isoquinolin-4-ium 3-oxide 

Relevant articles and documents

Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.

TfOH-Promoted Transition-Metal-Free Cascade Trifluoroethylation/Cyclization of Organic Isothiocyanates by Phenyl(2,2,2-trifluoroethyl)iodonium Triflate

An efficient and transition-metal-free method for the synthesis of the structurally diversified trifluoroethylthiol phenanthridines and 3,4-dihydroisoquinolines is described. Various 2-isothiocyanobiaryls and aryl alkyl isothiocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium triflate in CH2Cl2 in the presence of trifluoromethanesulfonic acid at 40 °C to form the corresponding trifluoroethylation/cyclization products in good to quantitative yields. This work represents the first construction of trifluoroethylthiol phenanthridine and isoquinoline derivatives from isothiocyanates in the absence of transition-metal catalysts by a one-pot procedure.

Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides

Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.

Oxidative Coupling-Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides

An efficient and selective multicomponent oxidative coupling, involving the use of two different amines, sodium phosphate, and elemental sulfur have been described for the preparation of thioamides, employing microwave irradiation. The use of an iron(III)-based imidazolium salt is essential as catalyst. Indeed, the iron-based catalyst is involved in the oxidative coupling of the two amines and in the subsequent C-S bond formation. The protocol is useful for a wide variety of primary benzylamines and alkylamines, as coupling partners. Thus, various electron-rich and electron-poor substituents in the aromatic rings and also fused piperidine derivatives, are suitable starting materials in this reaction. Some of the obtained products are important synthetic intermediates for natural products.

A multipathway coupled domino strategy: I2-mediated oxidative thionation for direct synthesis of thiobenzamides from miscellaneous substrates

An efficient iodine-mediated multipathway coupled domino reaction has been developed for the synthesis of thiobenzamides from benzylamines, benzylamines/aldehydes, and N-alkyl benzylamines under the same reaction conditions. This approach combines two consecutive domino processes in one pot using iodine as the oxidant.

Friedel-Crafts-type reactions with ureas and thioureas

Despite the relatively low reactivities of urea and thiourea functional groups towards nucleophilic attack, we have found conditions in which they are useful substrates in Friedel-Crafts reactions. The Bronsted superacid, triflic acid, promotes these reactions and a mechanism is proposed involving dicationic, superelectrophilic intermediates.

Microwave-assisted synthesis of thioamides with elemental sulfur

Thioamides are prepared in moderate-to-good yields from the benzylamines or benzylamine derivatives by treatment with elemental sulfur under microwave and solvent-free conditions at 170.C in 15 min.

P4S10/dimethicone tandem: Efficient reagent for thionation of various aromatic amides and esters

Organosulfur compounds are valuable because of their rich and varied chemistry especially in biological field. We report a new and efficient way for thionation of various aromatic amides and esters using P4S 10/ dimethicone tandem. The ease of handling and higher yield makes this protocol economical.

Synthesis of novel tricyclic aryltriazole-3-thione compounds

A new synthetic protocol has been developed to provide entry into a series of novel tricyclic aryltriazole-3-thiones analogs. The classical reaction conditions of subjecting an arylhydrazide with thiophosgene to form the thioisocyanate intermediate and ultimately the corresponding aryltriazole-3-thione framework were not successful. However, using a combination of carbon disulfide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to form the thioisocyanate intermediate was found to produce the novel tricyclic aryltriazole-3-thiones (5, 8a-c) in good yield. Copyright Taylor & Francis, Inc.

Reactions of 1,2,3,4-Tetrahydroisoquinoline Derivatives with Sulfur

1,2,3,4-Tetrahydroisoquinolines react with sulfur in pyridine to give two different types of products, depending on the structure of the starting compounds. 1-Substituted derivatives 1 undergo partial dehydrogenation with formation of the corresponding 3,4-dihydroisoquinolines 3. 1,2,3,4-Tetrahydroisoquinolines 5 bearing no substituent in 1-position yield the 3,4-dihydro-1(2H)isoquinolinethiones 6, comprising a new and simple synthesis of compounds 6.