3230-65-7

Basic information

• Product Name: 3,4-DIHYDROISOQUINOLINE
• Synonyms: 3,4-DIHYDROISOQUINOLINE;AKOS 213-252;3,4-Dihydroisoquinoline ,97%;Isoquinoline, 3,4-dihydro-;3,4-Dihydroisoquinoline >=97.5% (GC)
• CAS NO: 3230-65-7
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 221-769-0
• Mol File: 3230-65-7.mol
• Article Data: 175

Chemical Properties

• Melting Point: 251-254℃
• Boiling Point: 241.8±20.0℃ (760 Torr)
• Flash Point: 91.6±22.6℃
• Appearance: /
• Density: 1.05±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0548mmHg at 25°C
• Refractive Index: 1.6041 (589.3 nm 30℃)
• Storage Temp.: 2-8°C
• PKA: 5.80±0.20(Predicted)
• CAS DataBase Reference: 3,4-DIHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDROISOQUINOLINE(3230-65-7)
• EPA Substance Registry System: 3,4-DIHYDROISOQUINOLINE(3230-65-7)

Safety Data

• Hazard Codes: T
• Statements: 22-24-36/38
• Safety Statements: 26-36/37-45
• RIDADR: UN 2811 6.1 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 3230-65-7(Hazardous Substances Data)

Usage

Description

3,4-Dihydroisoquinoline is an organic compound derived from 1,2,3,4-Tetrahydroisoquinoline (T293820) and is characterized by its bicyclic structure with a nitrogen atom in the ring. It serves as a versatile intermediate in the synthesis of various pharmaceutical compounds and organic molecules.

Uses

Used in Pharmaceutical Industry:
3,4-Dihydroisoquinoline is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, which are antiproliferative tubulin inhibitors. These compounds have potential applications in the development of anticancer drugs.
Used in Organic Synthesis:
3,4-Dihydroisoquinoline can be used as a reactant to synthesize various organic compounds, such as:
5,6-Dihydro-8H-isoquino[1,2-b]quinazolin-8-one: 3,4-DIHYDROISOQUINOLINE is synthesized through a decarboxylative cyclization reaction with isatoic anhydride using tetrabutylammonium iodide (TBAI) as a catalyst.
1-naphtholyl tetrahydroisoquinoline: 3,4-DIHYDROISOQUINOLINE is synthesized through an aza-Friedel-Crafts reaction with various naphthols, which can be used in the development of organic dyes and pigments.
3,4-dihydroisoquinoline pseudo bases: These are employed as starting materials for the preparation of 3-benzazepine derivatives, which have potential applications in the synthesis of pharmaceutical compounds and other organic molecules.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6567, 1994 DOI: 10.1016/S0040-4039(00)78274-8

InChI:InChI=1/C9H9N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,7H,5-6H2

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 198973-60-3 N-chlorotetrahydroisoquinoline 
• 493-05-0 isochromane 
• 124-38-9 carbon dioxide 
• 14028-67-2 N-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 71-43-2 benzene 
• 108-88-3 toluene 
• 56-23-5 tetrachloromethane 
• 10025-87-3 trichlorophosphate 
• 10026-13-8 phosphorus pentachloride 
• 119-64-2 tetralin 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 116956-99-1 2-(2,4-dinitro-phenyl)-3,4-dihydro-isoquinolinium; chloride . compound with 3,4-dihydro-isoquinoline 
• 10166-05-9 4-benzylisoquinoline 
• 119-65-3 isoquinoline 
• 62541-59-7 7-nitro-3,4-dihydroisoquinoline 
• 129818-76-4 1-(3-hydroxy-2-cyclohexen-1-on-2-yl)-2-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 110254-47-2 1-Diacetylmethyl-2,3-diphenyl-5,6-dihydropyrrolo<2.1-a>isochinolin 
• 74156-45-9 2-(2-Chloromethyl-benzoyl)-1,2,3,4-tetrahydro-isoquinoline-1-carbonitrile 
• 105400-81-5 2-(1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acid 
• 1424-84-6 1-(ethoxycarbonylmethyl)-1,2,3,4-tetrahydroisoquinoline 
• 90136-99-5 4-(p-hydroxybenzyl)-isoquinoline 
• 90136-93-9 4-(o-hydroxybenzyl)-isoquinoline 
• 67438-80-6 1-(5,5-dimethyl-3-hydroxy-2-cyclohexen-1-on-2-yl)-2-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 129818-88-8 1-(5,5-dimethyl-3-hydroxy-2-cyclohexen-1-on-2-yl)-2-benzoyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

A one-pot catalyst/external oxidant/solvent-free cascade approach to pyrimidines: Via a 1,5-hydride transfer

A cascade 3-component reaction of 6-aminouracil, aldehyde and tetrahydroisoquinolines under heating in the absence of catalyst, external oxidant and solvent is performed. The reaction constructs a new pyrimidine ring by the functionalization of the C-H bond adjacent to nitrogen through a 1,5-hydride shift. No chromatographic techniques were required to purify the products.

Investigation of the regio- and stereoselectivity of the annelation reaction of cyclic Schiff base with structurally asymmetrical β,β′-triketones. Synthesis and properties of 17-acetoxy-8-aza-D-Homogona-12,17a-diones

Annelation ([2+4]-cyclocondensation) of 3,4-dihydroixoquinolines and 2-acetyl-4-acetoxycyclohexane-1,3-dione gives 17-acetoxy-8-aza-D-homogona-12,17a-diones as a mixture of the C(9), C(17)-stereoisomers with the (9R, 17S: 9S, 17R) racemic pair predominating.

Stereochemistry and Mechanistic Insight in the [2k+2i+2i] Annulations of Ketenes and Imines

The stereochemistry and mechanistic insight in the annulations of one ketene molecule with two imine molecules ([2k+2i+2i] annulation) are studied by using six-membered 3,4-dihydroisoquinoline as an imine probe. A concerted hetero-Diels-Alder cycloaddition mechanism is proposed to explain the stereochemical outcomes. In most cases, the zwitterionic 2-aza-1,3-butadiene-type intermediates, generated from ketenes and imines, undergo endo hetero-Diels-Alder cycloaddition with the second imine molecule. For ketenes with electron-donating substituents, (2,4)-cis-(4,5)-cis-[2k+2i+2i] annuladducts formed stereospecifically, while, for ketenes with electron-accepting substituents, (2,4)-cis-(4,5)-trans-[2k+2i+2i] annuladducts are generated stereospecifically. The [2k+2i+2i] annulations of aryloxyketenes and 3,4-dihydroisoquinoline give stereodivergent products due to the occurrence of the stepwise nucleophilic annulation. However, in the [2k+2i+2i] annulations of seven-membered cyclic imine dibenzo[b,f][1,4]oxazepine, the zwitterionic aza-butadiene-type intermediates exclusively undergo exo hetero-Diels-Alder cycloadditions with another molecule of imine to yield (2,4)-trans-(4,5)-trans-[2k+2i+2i] annuladducts stereospecifically, regardless of the ketene substituents. The mechanistic model not only discloses the nature of the [2k+2i+2i] annulations, but also can be used to explain and predict the stereochemistry of the [2k+2i+2i] annuladducts from different ketenes and imines.

Synthesis and properties of a chiral bis-tetrahydroisoquinoline proton sponge

A new chiral proton sponge has been prepared, and the reasons for its unusually high basicity elucidated by a quantum chemical study.

Peganumine A alkaloid structure simplifier and application thereof

The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.

Aprotic Amine-modified Manganese Dioxide Catalysts for Selectivity-tunable Oxidation of Amines

Organic modifiers have shown promising potential for regulating the activity and selectivity of heterogeneous catalysts via tuning their surface properties. Despite the increasing application of organic modification technique in regulating the redox-acid