Bifendate

Base Information

• Chemical Name: Bifendate
• CAS No.: 73536-69-3
• Molecular Formula: C₂₀H₁₈O₁₀
• Molecular Weight: 418.357
• Hs Code.: 2932992000
• UNII: 0G32E321W1
• DSSTox Substance ID: DTXSID40223736
• Nikkaji Number: J410.695D
• Wikidata: Q27236735
• Metabolomics Workbench ID: 121266
• ChEMBL ID: CHEMBL105184
• Mol file: 73536-69-3.mol

Synonyms:7,7'-dimethoxy-(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid dimethyl ester;alpha-diphenyldicarboxylate;BDD;biphenyl dimethyl-dicarboxylate;dimethyl 4,4'-dimethoxy-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-dicarboxylate;dimethyl diphenyl bicarboxylate;diphenyl dimethyl dicarboxylate

Chemical Property of Bifendate

Chemical Property:

• Vapor Pressure: 1.12E-14mmHg at 25°C
• Melting Point: 179-181 °C
• Refractive Index: 1.579
• Boiling Point: 606.9 °C at 760 mmHg
• Flash Point: 265.9 °C
• PSA: 107.98000
• Density: 1.39 g/cm³
• LogP: 2.40140
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 418.08999677
• Heavy Atom Count: 30
• Complexity: 587

Purity/Quality:

99% ^*data from raw suppliers

Bifendate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C(=C(C(=C1)C(=O)OC)C3=C4C(=C(C=C3C(=O)OC)OC)OCO4)OCO2
• Uses: Bifendate is a synthetic intermediate of Schisandrin C and also a anti-HBV drug used in the treatment of chronic hepatitis B.

Technology Process of Bifendate

There total 20 articles about Bifendate 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: 85.0%

4-bromo-7-methoxybenzo[1,3]dioxole-5-carboxylic acid methyl ester (81474-46-6) → DDB (111897-19-9,111897-25-7,111897-26-8,73536-69-3)

Guidance literature:

With copper; In N,N-dimethyl-formamide; at 180 ℃; for 16h;

DOI:10.1016/j.tet.2004.11.083

Reference yield:

5-methoxy-3,4-dihydroxy-2-bromobenzoic acid methyl ester (123685-25-6) → DDB (111897-19-9,111897-25-7,111897-26-8,73536-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / potassium fluoride / dimethylformamide / 110 °C

2: 85 percent / copper / dimethylformamide / 16 h / 180 °C

With potassium fluoride; copper; In N,N-dimethyl-formamide; 2: Ullmann coupling;

DOI:10.1016/j.tet.2004.11.083

Reference yield:

methyl galloate (99-24-1) → DDB (111897-19-9,111897-25-7,111897-26-8,73536-69-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 98.5 percent / Amberlyst 15E / benzene / 18 h / Heating

2: potassium carbonate / dimethylformamide / 12 h / 70 °C

3: hydrochloric acid / methanol; H₂O / 2 h / 20 °C

4: 98 percent / 1,3-dibromo-5,5-dimethylhydantoin / CHCl₃ / 24 h / 20 °C

5: 84 percent / potassium fluoride / dimethylformamide / 110 °C

6: 85 percent / copper / dimethylformamide / 16 h / 180 °C

With hydrogenchloride; potassium fluoride; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; Amberlyst 15E; copper; potassium carbonate; In methanol; chloroform; water; N,N-dimethyl-formamide; benzene; 6: Ullmann coupling;

DOI:10.1016/j.tet.2004.11.083

upstream raw materials:

4-bromo-7-methoxybenzo[1,3]dioxole-5-carboxylic acid methyl ester

methanol

7,7'-Dimethoxy-[4,4']bi[benzo[1,3]dioxolyl]-5,5'-dicarboxylic acid bis-((S)-2-acetylamino-propyl) ester

3,4,5-trihydroxybenzoic acid

Downstream raw materials:

(3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-diyl)bis(methylene) dibenzoate

(E)-methyl 5'-(3-(2,5-dimethoxyphenyl)-3-oxoprop-1-en-1-yl)-7,7'-dimethoxy-(4,4'-bibenzo[d][1,3]dioxole)-5-carboxylate

(E)-methyl 5'-(3-(2,4-dimethoxyphenyl)-3-oxoprop-1-en-1-yl)-7,7'-dimethoxy-{4,4'-bibenzo[d][1,3]dioxole}-5-carboxylate

(E)-methyl 7,7'-dimethoxy-5'-(3-(2-methoxyphenyl)-3-oxoprop-1-en-1-yl)-(4,4'-bibenzo[d][1,3]dioxole)-5-carboxylate

Refernces

• 1、 Tan, Qitao,Li, Hongyan,Wen, Jiwu,Jiang, Chen,Wang, Xin,You, Tianpa. "Asymmetric synthesis of β-DDB through oxazoline-mediated Ullmann coupling". . p. 2289 - 2296. Retrieved 2007/10/03.
• 2、 Chang, Junbiao,Chen, Rongfeng,Guo, Ruiyun,Dong, Chunhong,Zhao, Kang. "Synthesis, separation, and theoretical studies of chiral biphenyl lignans (α- and β-DDB)". . p. 2239 - 2246. Retrieved 2007/10/03.