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

Uses

Different sources of media describe the Uses of 3230-65-7 differently. You can refer to the following data:
1. 3,4-Dihydroisoquinoline is derived from 1,2,3,4-Tetrahydroisoquinoline (T293820), which is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides as antiproliferative tubulin inhibitors.
2. 3,4-Dihydroisoquinoline can be used as a reactant to synthesize: 5,6-Dihydro-8H-isoquino[1,2-b]quinazolin-8-one by decarboxylative cyclization reaction with isatoic anhydride using tetrabutylammonium iodide (TBAI). 1-naphtholyl tetrahydroisoquinoline by aza-Friedel-Crafts reaction with various naphthols. 3,4-dihydroisoquinoline pseudo bases, which are employed as starting materials for the preperation of 3-benzazepine derivatives.

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 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 60355-20-6 2'-(2-chloroethyl)benzaldehyde 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 75-18-3 dimethylsulfide 
• 100-68-5 methyl-phenyl-thioether 
• 139-66-2 diphenyl sulfide 
• 1822-73-7 phenylthioethylene 
• 7647-01-0 hydrogenchloride 
• 198973-60-3 N-chlorotetrahydroisoquinoline 
• 102-93-2 3-phenylpropionamide 
• 64-04-0 phenethylamine 
• 7783-06-4 hydrogen sulfide 
• 103-69-5 N-ethyl-N-phenylamine 

Downstream Products

• 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 
• 129818-87-7 1-(5,5-dimethyl-3-hydroxy-2-cyclohexen-1-on-2-yl)-2-propionyl-1,2,3,4-tetrahydroisoquinoline 
• 129818-89-9 1-(5,5-dimethyl-3-hydroxy-2-cyclohexen-1-on-2-yl)-2-chloroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 30345-80-3 1-(o-methylbenzyl)-1,2,3.4-tetrahydroisoquinoline 
• 19716-56-4 1-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 77014-20-1 2-Phenylamino-1,6,7,11b-tetrahydro-pyrido[2,1-a]isoquinolin-4-one 

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.

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

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.