479-59-4

Basic information

• Product Name: Julolidine
• Synonyms: JULOLIDINE;2,3,6,7-TETRAHYDRO-1H,5H-BENZO[IJ]QUINOLIZINE;2,3,6,7-TETRAHYDRO-1H,5H-PYRIDO[3.2.1-IJ]QUINOLINE;1H,5H-BENZO[IJ]QUINOLIZINE, 2,3,6,7-TETRAHYDRO-;5h-benzo[ij]quinolizine,2,3,6,7-tetrahydro-1;Julolidine,98%;2,3,6,7-Tetrahydro-1H,5H-benzop[ij]quinolizine;Julolidine, 98% 25GR
• CAS NO: 479-59-4
• Molecular Formula: C₁₂H₁₅N
• Molecular Weight: 173.25
• EINECS: 207-535-0
• Product Categories: Miscellaneous Natural Products
• Mol File: 479-59-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 34-36 °C(lit.)
• Boiling Point: 170-173°C 31mm
• Flash Point: >230 °F
• Appearance: Clear yellow to orange-brown/Liquid After Melting
• Density: 1.0030
• Vapor Pressure: 0.000554mmHg at 25°C
• Refractive Index: 1.5680
• Storage Temp.: 0-6°C
• PKA: 6.54±0.20(Predicted)
• Water Solubility: Soluble in toluene. Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 139925
• CAS DataBase Reference: Julolidine(CAS DataBase Reference)
• NIST Chemistry Reference: Julolidine(479-59-4)
• EPA Substance Registry System: Julolidine(479-59-4)

Safety Data

• Statements: 52/53
• Safety Statements: 24/25-61
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 479-59-4(Hazardous Substances Data)

Usage

Description

Julolidine is an organic compound that serves as a crucial amine building block in the synthesis of various materials and compounds. It is characterized by its unique chemical structure and properties, which make it versatile for a wide range of applications across different industries.

Uses

Used in Chemical Synthesis:
Julolidine is used as an amine building block for the creation of chemoluminescent dyes, photoconductive materials, and nonlinear optical materials. Its chemical structure allows for the development of these advanced materials with specific properties tailored for various applications.
Used in Analytical Chemistry:
In the field of analytical chemistry, Julolidine is utilized as a chromogenic substrate in redox reactions. Its ability to change color upon interaction with other chemicals makes it a valuable tool for detecting and measuring the presence of specific substances.
Used in Pharmaceutical Research:
Julolidine holds potential in the development of antidepressants and tranquilizers due to its chemical properties. Its structure can be modified to target specific receptors in the brain, potentially leading to the creation of new and more effective medications for mental health disorders.
Used in Photography:
Julolidine is employed in the photography industry to improve color stability. Its incorporation into photographic materials helps enhance the durability and longevity of colors in printed images, ensuring that they remain vibrant and true to life over time.
Used in High Sensitivity Photopolymerization:
In the field of materials science, Julolidine is used in the development of high sensitivity photopolymerizable materials. These materials have the ability to rapidly change their properties when exposed to light, making them ideal for applications such as 3D printing and other advanced manufacturing processes.

Purification Methods

Purify julolidine by dissolving it in dilute HCl, steam is bubbled through the solution and the residual acidic solution is basified with 10N NaOH, extracted with Et2O, washed with H2O, dried (NaOH pellets), filtered, evaporated and distilled in vacuo. The distillate crystallises on cooling (m 39-40o). It develops a red colour on standing in contact with air for several days. The colour can be removed by distilling or dissolving in 2-3 parts of hexane, adding charcoal, filtering and cooling in an Me2CO/Dry-ice bath when julolidine crystallises out (85-90% yield m 39-40o). The hydrobromide [83646-41-7] has m 218o (239-242o), the picrate has m 174o(165o) and the methiodide crystallises from MeOH, with m 186o [Glass & Weisberger Org Synth Coll Vol III 504 1955, Smith & Yu J Org Chem 17 1285 1952, Beilstein 20 H 332, 20 I 133, 20 II 214, 20 III/IV 3281.] Highly TOXIC.

InChI:InChI=1/C12H15N/c1-4-10-6-2-8-13-9-3-7-11(5-1)12(10)13/h1,4-5H,2-3,6-9H2

Upstream product

• 109-70-6 1.3-chlorobromopropane 
• 62-53-3 aniline 
• 100-61-8 N-methylaniline 
• 103-70-8 Formanilid 
• 504-63-2 trimethyleneglycol 
• 31121-11-6 3-hydroxy-N-phenylpropylamine 
• 106-49-0 p-toluidine 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 41175-50-2 8-hydroxyjulolidine 
• 56-23-5 tetrachloromethane 
• 5279-24-3 3-[(3-hydroxypropyl)anilino]-1-propanol 
• 88014-20-4 3-(1,2,3,4-tetrahydro-1-quinolyl)-1-propanol 
• 127395-14-6 Bis-benzotriazol-1-ylmethyl-phenyl-amine 
• 109-92-2 ethyl vinyl ether 

Downstream Products

• 201533-79-1 [4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)benzylidene]propanedinitrile 
• 1352574-11-8 4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)benzaldehyde 
• 1219458-66-8 C₂₂H₂₅N₃O₃S 
• 1219458-48-6 C₂₄H₂₃N₃O₂S 
• 1219458-45-3 C₂₅H₂₅N₃O₂S 
• 33985-71-6 9-julolidinecarboxaldehyde 
• 101077-29-6 9-hydroxymethyl-4-methyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolinium; iodide 
• 405168-04-9 1-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)-2-(2-carboxybenzamido)ethanone 
• 6310-83-4 9-formyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine oxime 

Relevant articles and documents

Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines

The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.

Iridium-Catalyzed Sustainable Access to Functionalized Julolidines through Hydrogen Autotransfer

The straightforward and ecofriendly preparation of functionalized julolidines starting from tetrahydroquinoline, diols, and aldehydes, for which water is produced as the only side product was investigated. To achieve this task, several well-defined ruthenium and iridium complexes including three new complexes were prepared from the corresponding phosphine-sulfonates, phosphine-carboxylates, and phosphine-phosphonates. The first transformation involved in situ generation of enaminoiminium intermediates, which allowed the formation of the julolidines through formal N,C(sp2)-cyclization of tetrahydroquinoline and the propane-1,3-diols. The influence of the chelate acidity points out that [Cp?IrIII]-based catalysts (Cp?=C5Me5) featuring phosphine-carboxylate and phosphine-sulfonate ligands were suitable for the cyclization, whereas the acidic phosphinophosphonate-containing complex favored the formation of reduced N-alkylated tetrahydroquinoline. We found that substitution of the propane-1,3-diols was crucial for the generation of enaminoiminium ions, which accounts for the efficiency and selectivity of the reaction. Applying another hydrogen autotransfer process, the prepared julolidines were easily functionalized at the C2 position.

A traceless perfluoroalkylsulfonyl (PFS) linker for the deoxygenation of phenols

(Equation presented) The synthesis of a novel perfluoroalkylsulfonyl (PFS) fluoride is described for use as a traceless linker in solid-phase organic synthesis. Attachment to the resin and subsequent coupling of a phenol affords a stable arylsulfonate that behaves as a support-bound aryl triflate. Palladium-mediated reductive cleavage of a wide variety of phenols generated the parent arenes. The resin-bound aryl triflate was shown to be stable to reductive amination conditions, and the traceless synthesis of Meclizine is reported.