Julolidine

Base Information

• Chemical Name: Julolidine
• CAS No.: 479-59-4
• Molecular Formula: C12H15N
• Molecular Weight: 173.258
• Hs Code.: 29339900
• European Community (EC) Number: 207-535-0
• NSC Number: 82354
• UNII: 8ERL3KJ6GQ
• DSSTox Substance ID: DTXSID0060060
• Nikkaji Number: J12.518K
• Wikipedia: Julolidine
• Wikidata: Q6310392
• ChEMBL ID: CHEMBL1899731
• Mol file: 479-59-4.mol

Synonyms:Julolidine;479-59-4;1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinoline;2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine;1H,5H-Benzo[ij]quinolizine, 2,3,6,7-tetrahydro-;2,3,6,7-Tetrahydro-1H,5H-benzo(ij)quinolizine;2,3,6,7-Tetrahydro-1H,5H-benzo[i,j]quinolizine;8ERL3KJ6GQ;2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline;EINECS 207-535-0;1H,5H-Benzo(ij)quinolizine, 2,3,6,7-tetrahydro-;MFCD00006917;NSC 82354;NSC-82354;1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8-triene;NSC82354;Julolidine, 97%;UNII-8ERL3KJ6GQ;SCHEMBL60540;CHEMBL1899731;DTXSID0060060;AKOS005062871;DS-6638;NCGC00188119-01;NCGC00188119-02;NCGC00188119-03;AC-11756;SY049266;CS-0128844;FT-0627560;J0007;2,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine;A18806;D70103;J-1000;EN300-2007996;Q6310392;1-azatricyclo[7.3.1.0,5,13]trideca-5,7,9(13)-triene;2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline #

Chemical Property of Julolidine

Chemical Property:

• Appearance/Colour: Clear yellow to orange-brown liquid after melting
• Vapor Pressure: 0.000554mmHg at 25°C
• Melting Point: 34-36 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 311.7 °C at 760 mmHg
• PKA: 6.54±0.20(Predicted)
• Flash Point: 129.6 °C
• PSA: 3.24000
• Density: 1.1 g/cm³
• LogP: 2.45040
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in toluene. Insoluble in water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 173.120449483
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

Julolidine ^*data from reagent suppliers

Safty Information:

• Statements: 52/53
• Safety Statements: 24/25-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2=C3C(=CC=C2)CCCN3C1
• Uses: Julolidine used as amine building block and in chemoluminescent dye. Also used in photoconductive materials, chemiluminescence substances, chromogenic substrates in analytical redox reactions, dye intermediates, potential antidepressants and tranquilizers, nonlinear optical materials, high sensitivity photopolymerizable materials, and for improving color stability in photography.

Technology Process of Julolidine

There total 29 articles about Julolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + trimethyleneglycol (504-63-2) → julolidine (479-59-4)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; ortho-diphenylphosphinobenzoic acid; In toluene; at 130 ℃; for 36h; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1002/cctc.201500051

Reference yield: 80.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + trimethyleneglycol (504-63-2) → julolidine (479-59-4) + 1-propyl-1,2,3,4-tetrahydroquinoline (6613-29-2)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; ortho-diphenylphosphinobenzoic acid; In toluene; at 130 ℃; for 36h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1002/cctc.201500051

Reference yield: 74.0%

8-hydroxyjulolidine (41175-50-2) → julolidine (479-59-4)

Guidance literature:

8-hydroxyjulolidine; With TentaGel-N(R)C(O)CH₂C₂F₄OC₂F₄SO₂F; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

With formic acid; 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate; In N,N-dimethyl-formamide; at 85 ℃; for 2h; Further stages.;

DOI:10.1021/ol0163732

upstream raw materials:

1,2,3,4-tetrahydroisoquinoline

1.3-chlorobromopropane

6,7-dihydropyrido[3,2,1-ij]quinoline-1,3(2H,5H)-dione

3-[(3-hydroxypropyl)anilino]-1-propanol

Downstream raw materials:

9-julolidinecarboxaldehyde

4-methyl-2,3,6,7-tetrahydro-1H,5H-pyrido [3.2.1-ij] quinolinium iodide

9-bromo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline

9-(4-nitrophenylazo)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline

Refernces

• 1、 Minakawa, Maki,Watanabe, Kouichi,Toyoda, Satoru,Uozumi, Yasuhiro. "Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols". supporting information. p. 2385 - 2389. Retrieved 2018/11/23.
• 2、 Shao, Jingyin,Ji, Shaomin,Li, Xiaolian,Zhao, Jianzhang,Zhou, Fuke,Guo, Huimin. "Thiophene-inserted aryl-dicyanovinyl compounds: The second generation of fluorescent molecular rotors with significantly redshifted emission and large stokes shift". supporting information; experimental part. p. 6100 - 6109. Retrieved 2011/12/03.