1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE

Base Information

• Chemical Name: 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE
• CAS No.: 101432-05-7
• Molecular Formula: C16H18O4
• Molecular Weight: 274.317
• Mol file: 101432-05-7.mol

Synonyms:4,4'-Butandiyl-di-brenzcatechin;1.4-Bis-(3.4-dihydroxy-phenyl)-butan;1,4-bis(catechol-4-yl)-butane;1,2-Benzenediol,4,4'-(1,4-butanediyl)bis;4,4'-butanediyl-di-pyrocatechol;1,4-bis-(3,4-hydroxyphenyl) butane;1,4-bis (3,4-dihydroxyphenyl)butane;

Chemical Property of 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE

Chemical Property:

• PSA: 80.92000
• LogP: 3.07440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE

There total 23 articles about 1,4-BIS(3,4-DIHYDROXYPHENYL)BUTANE 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: 100.0%

1,4-bis(3,4-dimethoxyphenyl)butane (51487-58-2) → 4,4’-(butane-1,4-diyl)bis(benzene-1,2-diol) (101432-05-7)

Guidance literature:

With boron tribromide;

Reference yield: 56.0%

4-[4-(3,4-dimethoxyphenyl)butyl]benzene-1,2-diol → 4,4’-(butane-1,4-diyl)bis(benzene-1,2-diol) (101432-05-7)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2019.111910

Reference yield:

4-(3,4-dimethoxyphenyl)butanoic acid (13575-74-1) → 4,4’-(butane-1,4-diyl)bis(benzene-1,2-diol) (101432-05-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / lithium aluminum hydride / tetrahydrofuran / 3.5 h / 20 °C

2: 77 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

3: 76 percent / tetrahydrofuran / -78 - 20 °C

4: 62 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

5: hydrazine hydrate / ethanol / 4 h / Heating

6: 0.0154 g / potassium t-butoxide / dimethylsulfoxide / 20 h / 20 °C

7: 0.072 g / aq. NaOH / methanol / 1 h / 100 °C

8: 47 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydroxide; lithium aluminium tetrahydride; potassium tert-butylate; boron tribromide; hydrazine hydrate; pyridinium chlorochromate; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2007.04.092

upstream raw materials:

1,4-bis-benzo[1,3]dioxol-5-yl-butane

1,4-bis(3,4-dimethoxyphenyl)butane

4-(3,4-dimethoxyphenyl)butanoic acid

1-(3,4-dichlorophenyl)-4-(3,4-dimethoxyphenyl)butan-1-ol

Downstream raw materials:

1,4-bis{3,4-bis[2-(1-methyl-piperazin-4-yl)-ethoxy]phenyl}-butane

1,4-bis{3,4-bis[3-(piperidin-1-yl)propoxy]phenyl}-butane

1,4-bis{3,4-bis(2-(N,N'-dimethylamino)-ethoxy)phenyl}-butane

1,4-bis-(3,4-ethoxyphenyl) butane

Refernces

• 1、 Asiamah, Isaac,Hodgson, Heather L.,Maloney, Katherine,Allen, Kevin J.H.,Krol, Ed S.. "Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues". supporting information. p. 7007 - 7014. Retrieved 2015/11/11.
• 2、 Blecha, Joseph E.,Anderson, Marc O.,Chow, Jennifer M.,Guevarra, Christle C.,Pender, Celia,Penaranda, Cristina,Zavodovskaya, Marianna,Youngren, Jack F.,Berkman, Clifford E.. "Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs". . p. 4026 - 4029. Retrieved 2008/02/12.