1-Pentylnaphthalene

Base Information

• Chemical Name: 1-Pentylnaphthalene
• CAS No.: 86-89-5
• Molecular Formula: C15H18
• Molecular Weight: 198.308
• DSSTox Substance ID: DTXSID30957816
• Nikkaji Number: J191.594K
• Mol file: 86-89-5.mol

Synonyms:1-Pentylnaphthalene;Naphthalene, 1-pentyl-;1-amylnaphthalene;DTXSID30957816;AKOS006274214

Chemical Property of 1-Pentylnaphthalene

Chemical Property:

• Melting Point: -26 °C
• Boiling Point: 164-165 °C(Press: 19 Torr)
• PSA: 0.00000
• Density: 0.963±0.06 g/cm3(Predicted)
• LogP: 4.57250
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 198.140850574
• Heavy Atom Count: 15
• Complexity: 173

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=CC=CC2=CC=CC=C21

Technology Process of 1-Pentylnaphthalene

There total 5 articles about 1-Pentylnaphthalene 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:

(E)-1-{1-acetoxy-3-[dimethyl(vinyl)silyl]prop-2-en-1-yl}naphthalene → 1-butylnaphthalene (1634-09-9) + 1-pentyl-naphthalene (86-89-5)

Guidance literature:

(E)-1-{1-acetoxy-3-[dimethyl(vinyl)silyl]prop-2-en-1-yl}naphthalene; With palladium diacetate; cesium fluoride; tris(para-trifluoromethyl)phenyl phosphine; In 1,4-dioxane; water; at 100 ℃; for 7h; Inert atmosphere;

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 12h; Overall yield = 165.1 mg;

DOI:10.1016/j.tet.2020.131493

Reference yield:

1-[3-(dimethylvinylsilyl)-1-(1-methoxy-1-methylethoxy)prop-2-yn-1-yl]naphthalene → 1-butylnaphthalene (1634-09-9) + 1-pentyl-naphthalene (86-89-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / tetrahydrofuran; water / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 0 - 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: tris(para-trifluoromethyl)phenyl phosphine; cesium fluoride; palladium diacetate / water; 1,4-dioxane / 7 h / 100 °C / Inert atmosphere

4.2: 12 h / 20 °C

With hydrogenchloride; dmap; palladium diacetate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; cesium fluoride; tris(para-trifluoromethyl)phenyl phosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/j.tet.2020.131493

Reference yield:

3-(dimethylvinylsilyl)-1-(naphthalen-1-yl)prop-2-yn-1-ol → 1-butylnaphthalene (1634-09-9) + 1-pentyl-naphthalene (86-89-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 0 - 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: tris(para-trifluoromethyl)phenyl phosphine; cesium fluoride; palladium diacetate / water; 1,4-dioxane / 7 h / 100 °C / Inert atmosphere

3.2: 12 h / 20 °C

With dmap; palladium diacetate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; cesium fluoride; tris(para-trifluoromethyl)phenyl phosphine; In 1,4-dioxane; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/j.tet.2020.131493

upstream raw materials:

methyl iodide

Refernces

• 1、 Ebden, Mark R.,Simpkins, Nigel S.,Fox, David N.A.. "Metallation of benzylic amines via amine-borane complexes". . p. 12923 - 12952. Retrieved 2007/10/03.