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 
• 42429-63-0 3,4-dihydroisoquinoline 1,2-oxide 
• 75-18-3 dimethylsulfide 
• 598-26-5 dimethylketene 
• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 54105-63-4 1,2,3,4-tetrahydroisoquinolin-2-ol 
• 2079-11-0 N-allyl 1,2,3,4-tetrahydroisoquinoline 
• 100-68-5 methyl-phenyl-thioether 
• 139-66-2 diphenyl sulfide 
• 1822-73-7 phenylthioethylene 
• 221102-37-0 1-carbethoxy-2-N,N-dimethylsulfamoyl-1,2,3,4-tetrahydroisoquinoline 

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 
• 66610-76-2 3-(2,2,6,6-tetramethyl-cyclohexylidene)-6,10b-dihydro-5H-[1,2,4]oxathiazolo[5,4-a]isoquinoline 
• 37760-44-4 3-phenyl-6,10b-dihydro-5H-[1,2,4]oxadiazolo[5,4-a]isoquinoline 
• 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 

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.

Enantioselective Allylation of Cyclic and In Situ Formed N-Unsubstituted Imines with Tetraol-Protected Allylboronates

Tetraol-protected α-chiral allylboronates are utilized in diastereo- and enantioselective transformations of cyclic imines (up to 98 %, d.r. 97 : 3, e.r. 99 : 1). An application to in situ formed N-unsubstituted imines gives in a consecutive one-pot sequence selective access to all four stereoisomers of the homoallylamine within minutes (up to 88 %, d.r. 81 : 19, e.r. 99 : 1). These results underline the usability, tuneability and stability of tetraol-based allylboronates.