4-(4-pentylbicyclo[2.2.2]oct-1-yl)benzonitrile

Base Information

• Chemical Name: 4-(4-pentylbicyclo[2.2.2]oct-1-yl)benzonitrile
• CAS No.: 74385-67-4
• Molecular Formula: C₂₀H₂₇N
• Molecular Weight: 281.441
• Mol file: 74385-67-4.mol

Synonyms:

Chemical Property of 4-(4-pentylbicyclo[2.2.2]oct-1-yl)benzonitrile

Chemical Property:

• Vapor Pressure: 1.51E-06mmHg at 25°C
• Boiling Point: 398.1°C at 760 mmHg
• Flash Point: 195.8°C
• Density: 1.02g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(4-pentylbicyclo[2.2.2]oct-1-yl)benzonitrile

There total 8 articles about 4-(4-pentylbicyclo[2.2.2]oct-1-yl)benzonitrile 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: 64.0%

copper(I) cyanide (544-92-3) + 1-(4-bromophenyl)-4-pentylbicyclo<2.2.2>octane (76921-48-7) → 4-pentyl-(4'-cyanophenyl)bicyclo-<2.2.2.>-octane (74385-67-4)

Guidance literature:

With hydrogenchloride; iron(III) chloride; 1.) 1-methyl-2-pyrrolidone, 185 deg C, 3h; 2.) water, 50-60 deg C, 20 min;

DOI:10.1039/P29810000026

Reference yield:

3-acetyl-1,5-dicyano-3-pentylpentane (34886-35-6) → 4-pentyl-(4'-cyanophenyl)bicyclo-<2.2.2.>-octane (74385-67-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / sodium hydroxide, water / 10 h / Heating

2: 71 percent / acetic anhydride / 14 h / Heating

3: 56 percent / potassium hydroxide, water / 6 h / 70 °C / Heating; 7

4: 82.7 percent / 1.) hydrazine hydrate;2.) potassium hydroxide, diethylene glycol / 1.) reflux, 5 h; 2.) 230 deg C - 240 deg C, 20 h

5: 95 percent / zinc bromide, 50percent hydrobromic acid / 16 h / 60 - 70 °C / Heating

6: 80 percent / 1.) anhydrous aluminium chloride; 2.) 15percent hydrochloric acid / nitrobenzene / 1.) 80 deg C; 2.) 20 min

7: 64 percent / 2.) anhydrous iron(III) chloride, HCl / 1.) 1-methyl-2-pyrrolidone, 185 deg C, 3h; 2.) water, 50-60 deg C, 20 min

With hydrogenchloride; potassium hydroxide; sodium hydroxide; aluminium trichloride; water; hydrogen bromide; acetic anhydride; iron(III) chloride; hydrazine hydrate; zinc dibromide; diethylene glycol; In nitrobenzene;

DOI:10.1039/P29810000026

Reference yield:

3-acetyl-3-pentylpentane-1,5-dicarboxylic acid (76921-70-5) → 4-pentyl-(4'-cyanophenyl)bicyclo-<2.2.2.>-octane (74385-67-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / acetic anhydride / 14 h / Heating

2: 56 percent / potassium hydroxide, water / 6 h / 70 °C / Heating; 7

3: 82.7 percent / 1.) hydrazine hydrate;2.) potassium hydroxide, diethylene glycol / 1.) reflux, 5 h; 2.) 230 deg C - 240 deg C, 20 h

4: 95 percent / zinc bromide, 50percent hydrobromic acid / 16 h / 60 - 70 °C / Heating

5: 80 percent / 1.) anhydrous aluminium chloride; 2.) 15percent hydrochloric acid / nitrobenzene / 1.) 80 deg C; 2.) 20 min

6: 64 percent / 2.) anhydrous iron(III) chloride, HCl / 1.) 1-methyl-2-pyrrolidone, 185 deg C, 3h; 2.) water, 50-60 deg C, 20 min

With hydrogenchloride; potassium hydroxide; aluminium trichloride; water; hydrogen bromide; acetic anhydride; iron(III) chloride; hydrazine hydrate; zinc dibromide; diethylene glycol; In nitrobenzene;

DOI:10.1039/P29810000026

upstream raw materials:

copper(I) cyanide

1-(4-bromophenyl)-4-pentylbicyclo<2.2.2>octane

3-acetyl-1,5-dicyano-3-pentylpentane

3-acetyl-3-pentylpentane-1,5-dicarboxylic acid