4,4''-Dimethoxy-1,1':4',1''-terphenyl

Base Information

• Chemical Name: 4,4''-Dimethoxy-1,1':4',1''-terphenyl
• CAS No.: 13021-19-7
• Molecular Formula: C20H18O2
• Molecular Weight: 290.362
• DSSTox Substance ID: DTXSID801310254
• Nikkaji Number: J764.118D
• Mol file: 13021-19-7.mol

Synonyms:13021-19-7;4,4''-DIMETHOXY-1,1':4',1''-TERPHENYL;1,1':4',1''-Terphenyl, 4,4''-dimethoxy-;1,4-bis(4-methoxyphenyl)benzene;4,4'-dimethoxyterphenyl;Dimethoxy-p-Terphenyl;4,4''-Dimethoxy-p-terphenyl;SCHEMBL6733562;DTXSID801310254;BCP32353;AKOS032947891;AM85551;CS-0182969;4,4''-Dimethoxy-[1,1';4',1'']terphenyl;4-methoxy-4'-(4-methoxyphenyl)-1,1'-biphenyl;1,4-Di(p-methoxyphenyl)benzene

Chemical Property of 4,4''-Dimethoxy-1,1':4',1''-terphenyl

Chemical Property:

• Melting Point: 272-275 °C(Solv: benzene (71-43-2))
• Boiling Point: 463.9±38.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.083±0.06 g/cm3(Predicted)
• LogP: 5.03780
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 290.130679813
• Heavy Atom Count: 22
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)OC

Technology Process of 4,4''-Dimethoxy-1,1':4',1''-terphenyl

There total 13 articles about 4,4''-Dimethoxy-1,1':4',1''-terphenyl 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: 58.0%

4-chlorophenyl p-toluenesulfonate (599-89-3) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 4,4-dimethoxy-1,1':4',1-terphenyl (13021-19-7) + 4′-methoxy-[1,1′-biphenyl]-4-yl 4-methylbenzenesulfonate (356031-48-6)

Guidance literature:

4-methoxyphenyl magnesium bromide; With titanium(IV) tetraethanolate; phenol; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

4-chlorophenyl p-toluenesulfonate; With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In tetrahydrofuran; toluene; at 20 - 78 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.9b00151

Reference yield: 30.0%

1.4-dibromobenzene (106-37-6) + 4-methoxyphenylboronic acid (5720-07-0) → 4-bromo-4'-methoxylbiphenyl (58743-83-2) + 4,4-dimethoxy-1,1':4',1-terphenyl (13021-19-7)

Guidance literature:

With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate; In water; at 80 ℃; for 1h;

DOI:10.3390/molecules25173993

Reference yield: 27.0%

1-bromo-4-methoxy-benzene (104-92-7) + benzene-1,4-diboronic acid bispinacol ester (99770-93-1) → 4,4-dimethoxy-1,1':4',1-terphenyl (13021-19-7) + 2-(4'-methoxy-[1,1,-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (446311-34-8)

Guidance literature:

With silver carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 16h; Heating;

DOI:10.1055/s-2002-25773

upstream raw materials:

1-bromo-4-methoxy-benzene

2,5-cyclohexadien-1-one

para-iodoanisole

1,4-Phenyldiboronic acid

Downstream raw materials:

4-<<4-(allyloxy)benzoyl>oxy>-4'-methoxy-p-terphenyl

1,4-bis[2-(4-hydroxyphenyl)-2-propylene]benzene

Refernces

• 1、 Todd, Matthew H.,Balasubramanian, Shankar,Abell, Chris. "Studies on the synthesis, characterisation and reactivity of aromatic diboronic acids". . p. 6781 - 6784. Retrieved 1997.
• 2、 Bunda, Szilvia,Joó, Ferenc,Kathó, ágnes,Udvardy, Antal,Voronova, Krisztina. "Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance". supporting information. . Retrieved 2020/09/18.
• 3、 Wang, Lei,Wei, Yi-Ming,Zhao, Yan,Duan, Xin-Fang. "Unified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents". . p. 5176 - 5186. Retrieved 2019/05/10.