1,1'-Biphenyl, 4-(3-butenyl)-4'-methyl-

Base Information

• Chemical Name: 1,1'-Biphenyl, 4-(3-butenyl)-4'-methyl-
• CAS No.: 117713-14-1
• Molecular Formula: C17H18
• Molecular Weight: 222.32500
• Mol file: 117713-14-1.mol

Synonyms:4-But-3-enyl-4'-methyl-biphenyl;

Chemical Property of 1,1'-Biphenyl, 4-(3-butenyl)-4'-methyl-

Chemical Property:

• Melting Point: 54 °C
• PSA: 0.00000
• LogP: 4.78060

Purity/Quality:

99.9% ^*data from raw suppliers

4-(3-Buten-1-yl)-4'-methylbiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1'-Biphenyl, 4-(3-butenyl)-4'-methyl-

There total 7 articles about 1,1'-Biphenyl, 4-(3-butenyl)-4'-methyl- 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: 92.35%

1-bromo-4-butene (5162-44-7) + 4-bromo-4'-methylbiphenyl (50670-49-0) → 4-(but-3-en-1-yl)-4'-methyl-1,1'-biphenyl (117713-14-1)

Guidance literature:

4-bromo-4'-methylbiphenyl; With iodine; magnesium; lithium chloride; In tetrahydrofuran; at 25 - 50 ℃; Inert atmosphere;

1-bromo-4-butene; With cobalt(II) aceylacetonate; In tetrahydrofuran; at 0 - 25 ℃; Reagent/catalyst; Solvent; Inert atmosphere;

Reference yield:

4-(4-iodobutyl)-4'-methyl-1,1'-biphenyl → 4-(but-3-en-1-yl)-4'-methyl-1,1'-biphenyl (117713-14-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1021/jacs.6bl0309

Reference yield:

4-(4-bromophenyl)butanoic acid (35656-89-4) → 4-(but-3-en-1-yl)-4'-methyl-1,1'-biphenyl (117713-14-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / 4 h / Reflux

2: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 24 h / 90 °C / Inert atmosphere

3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4: triphenylphosphine; 1H-imidazole; iodine / acetonitrile; diethyl ether / 1 h / 0 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / diethyl ether / 14 h / 20 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 1H-imidazole; potassium phosphate; lithium aluminium tetrahydride; sulfuric acid; iodine; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/jacs.6bl0309

upstream raw materials:

(4,4'-dimethyl-1,1'-biphenyl)

1,3-dibromo-propane

4-(4-bromophenyl)butanoic acid

4-(4-bromophenyl)butylic acid ethyl ester

Refernces

• 1、 Deb, Arghya,Hazra, Avijit,Peng, Qian,Paton, Robert S.,Maiti, Debabrata. "Detailed mechanistic studies on palladium-catalyzed selective C-H olefination with aliphatic alkenes: A significant influence of proton shuttling". . p. 763 - 775. Retrieved 2017/05/17.