Tetramethyl 3,3',4,4'-biphenyltetracarboxylate

Base Information

• Chemical Name: Tetramethyl 3,3',4,4'-biphenyltetracarboxylate
• CAS No.: 36978-37-7
• Molecular Formula: C20H18 O8
• Molecular Weight: 386.358
• Hs Code.: 2917399090
• DSSTox Substance ID: DTXSID60467099
• Nikkaji Number: J21.991F
• Wikidata: Q72507519
• Mol file: 36978-37-7.mol

Synonyms:36978-37-7;TETRAMETHYL 3,3',4,4'-BIPHENYLTETRACARBOXYLATE;3,3',4,4'-Biphenyl tetracarboxylic acid;Dimethyl 4-[3,4-bis(methoxycarbonyl)phenyl]benzene-1,2-dicarboxylate;tetramethyl (1,1'-biphenyl)-3,3',4,4'-tetracarboxylate;Tetramethyl [1,1'-biphenyl]-3,3',4,4'-tetracarboxylate;SCHEMBL6466451;DTXSID60467099;AS-77745;D93452;Tetramethyl[1,1'-biphenyl]-3,3',4,4'-tetracarboxylate

Chemical Property of Tetramethyl 3,3',4,4'-biphenyltetracarboxylate

Chemical Property:

• Melting Point: 93-101 ºC
• Boiling Point: 496.444oC at 760 mmHg
• Flash Point: 216.529oC
• PSA: 105.20000
• Density: 1.261
• LogP: 2.50000
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 386.10016753
• Heavy Atom Count: 28
• Complexity: 549

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=C(C=C(C=C1)C2=CC(=C(C=C2)C(=O)OC)C(=O)OC)C(=O)OC

Technology Process of Tetramethyl 3,3',4,4'-biphenyltetracarboxylate

There total 11 articles about Tetramethyl 3,3',4,4'-biphenyltetracarboxylate 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: 40.0%

phthalic acid dimethyl ester (131-11-3,64441-70-9) → 3,3',4,4'-biphenyltetracarboxylic acid tetramethyl ester (36978-37-7) + 2,3,3',4'-biphenyltetracarboxylic acid tetramethyl ester (36978-36-6)

Guidance literature:

Product distribution / selectivity;

Reference yield:

methanol (67-56-1) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) → 3,3',4,4'-biphenyltetracarboxylic acid tetramethyl ester (36978-37-7) + 2,3,3',4'-biphenyltetracarboxylic acid tetramethyl ester (36978-36-6) + biphenyltetracarboxylic acid tetramethyl ester (36978-38-8)

Guidance literature:

benzene-1,2-dicarboxylic acid; With chlorine; In water; for 3h;

methanol; for 1.5h; Alkaline conditions;

In N,N-dimethyl-formamide; at 60 ℃; for 5h;

Reference yield:

dimethyl 3-iodophthalate (102928-38-1) → 3,3',4,4'-biphenyltetracarboxylic acid tetramethyl ester (36978-37-7) + 2,3,3',4'-biphenyltetracarboxylic acid tetramethyl ester (36978-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 4 h / 50 °C

2: dichloromethane / 4 h / 20 °C

3: 0.5 h / 100 °C

4: copper(II) acetylacetonate; [Pd(OAc){C₆H₃(CO₂Me)₂-3,4}(phen)] / 6 h / 200 °C

With [Pd(OAc){C₆H₃(CO₂Me)₂-3,4}(phen)]; copper(II) acetylacetonate; In dichloromethane; benzene;

DOI:10.1021/acscatal.8b01095

upstream raw materials:

phthalic acid dimethyl ester

methanol

benzene-1,2-dicarboxylic acid

dimethyl 3-iodophthalate

Downstream raw materials:

3,3',4,4'-biphenyltetracarboxylic anhydride

4,4'-biphthalic acid

Refernces

• 1、 Kanazawa, Yuki,Mitsudome, Takato,Takaya, Hikaru,Hirano, Masafumi. "Pd/Cu-Catalyzed Dehydrogenative Coupling of Dimethyl Phthalate: Synchrotron Radiation Sheds Light on the Cu Cycle Mechanism". . p. 5909 - 5919. Retrieved 2020/05/18.
• 2、 Hirano, Masafumi,Sano, Kosuke,Kanazawa, Yuki,Komine, Nobuyuki,Maeno, Zen,Mitsudome, Takato,Takaya, Hikaru. "Mechanistic Insights on Pd/Cu-Catalyzed Dehydrogenative Coupling of Dimethyl Phthalate". . p. 5827 - 5841. Retrieved 2018/05/29.