Dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate

Base Information

• Chemical Name: Dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate
• CAS No.: 792-74-5
• Deprecated CAS: 156326-47-5
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• Hs Code.: 29173990
• European Community (EC) Number: 212-341-4
• UNII: K61BXA0U9C
• DSSTox Substance ID: DTXSID2061143
• Nikkaji Number: J56.222J
• Wikidata: Q27281994
• Metabolomics Workbench ID: 153459
• ChEMBL ID: CHEMBL4297409
• Mol file: 792-74-5.mol

Synonyms:792-74-5;Dimethyl biphenyl-4,4'-dicarboxylate;dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate;Biphenyl dimethyl dicarboxylate;DIMETHYL 4,4'-BIPHENYLDICARBOXYLATE;Nissel;methyl 4-(4-methoxycarbonylphenyl)benzoate;[1,1'-Biphenyl]-4,4'-dicarboxylic acid, dimethyl ester;4,4'-Biphenyldicarboxylic acid, dimethyl ester;UNII-K61BXA0U9C;K61BXA0U9C;HSDB 5754;Dimethyl (1,1'-biphenyl)-4,4'-dicarboxylate;4,4'-Bis(methoxycarbonyl)biphenyl;EINECS 212-341-4;4,4'-Bibenzoic Acid Dimethyl Ester;MFCD00017201;(1,1'-Biphenyl)-4,4'-dicarboxylic acid, dimethyl ester;dimethyl 4,4'-biphenyl-d8-dicarboxylate;1219803-50-5;Maybridge1_001712;4,4-Dicarboxymethylbiphenyl;4,4'-Dicarbomethoxybiphenyl;SCHEMBL68521;MLS000720058;CHEMBL4297409;DTXSID2061143;HMS546F18;(1,1'-Biphenyl)-4,4'-dicarboxylic acid, 4,4'-dimethyl ester;4,4'-bis (methoxycarbonyl)biphenyl;CCG-45472;AKOS001588888;DB12475;SMR000304587;SY057043;TS-00900;HY-128854;4,4-Biphenyldicarboxylic acid dimethyl ester;B1309;CS-0100928;Dimethyl biphenyl-4,4'-dicarboxylate, 99%;FT-0625049;Biphenyl-4,4'-dicarboxylic acid methyl ester;dimethyl[1,1'-biphenyl]-4,4'-dicarboxylate;4,4'-Biphenyldicarboxylic Acid Dimethyl Ester;F15436;Biphenyl 4,4'-dicarboxylic acid, dimethyl ester;A839634;SR-01000397421;SR-01000397421-1;SR-01000397421-2;W-111708;4,4'-dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate;BRD-K33126632-001-02-1;DIMETHYL 4,4'-BIPHENYLDICARBOXYLATE [WHO-DD];Q27281994;Dimethyl 4,4 inverted exclamation mark -Biphenyldicarboxylate;Dimethyl 4,4'-Biphenyldicarboxylate

Chemical Property of Dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate

Chemical Property:

• Appearance/Colour: White or cream crystalline powder
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Melting Point: 213-215 °C(lit.)
• Refractive Index: 1.555
• Boiling Point: 407 °C at 760 mmHg
• Flash Point: 204.7 °C
• PSA: 52.60000
• Density: 1.172 g/cm³
• LogP: 2.92680
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Benzene (Slightly, Heated, Sonicated), Chloroform (Slightly, Heated, Sonicated)
• Water Solubility.: Insoluble in water.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

4,4''-Bis(methoxycarbonyl)biphenyl ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C2=CC=C(C=C2)C(=O)OC
• Recent ClinicalTrials: Study to Evaluate Efficacy and Safety of PENNEL Capsule in the Patients With Chronic Liver Disease
• Uses: Dimethyl biphenyl-4,4'-dicarboxylate is used as a hepatoprotectant in the treatment of chronic hepatitis. At 250 μg/ml, it has been shown to stimulate JAK/STAT signaling and to induce the expression of interferon-α stimulated genes in a HepG2 cell line. It has been used to study hepatic fibrosis and chronic hepatocellular damage. It appears to normalize alanine aminotransferase (ALT) in cases where levels of ALT are elevated. It may be employed as starting reagent for the synthesis of dimethyl 2-fluoro-and 2,2?-difluorobiphenyl-4,4?-dicarboxylates.

Technology Process of Dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate

There total 112 articles about Dimethyl [1,1'-biphenyl]-4,4'-dicarboxylate 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: 99.0%

methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate (905966-40-7) + methyl 4-(methanesulfonyloxy)benzoate (161497-18-3) → 4,4'-biphenyldicarboxylic acid dimethyl ester (792-74-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium phosphate; tricyclohexylphosphine; In tetrahydrofuran; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo202037x

Reference yield: 99.0%

4-methoxycarbonylphenyl bromide (619-42-1) → 4,4'-biphenyldicarboxylic acid dimethyl ester (792-74-5)

Guidance literature:

With (1E,2E)-N¹,N²-bis(2,6-dimethylphenyl)ethane-1,2-diimine; nickel dibromide; zinc; In tetrahydrofuran; at 70 ℃; for 10h; Inert atmosphere;

DOI:10.1134/S1070428011110236

Reference yield: 99.0%

methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate (905966-40-7) + 4-methoxycarbonylphenyl bromide (619-42-1) → 4,4'-biphenyldicarboxylic acid dimethyl ester (792-74-5)

Guidance literature:

With potassium phosphate tribasic hydrate; Ni^IICl(1-naphthyl)(tricyclohexylphosphine)₂; tricyclohexylphosphine; In tetrahydrofuran; at 23 ℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1055/s-0035-1562342

upstream raw materials:

methyl 4-iodobenzoate

methanol

4,4'-diphenic acid

biphenyl

Downstream raw materials:

[1,1’-biphenyl]-4,4’-diylbis(diphenylmethanol)

4,4'-Bis-(α-hydroxy-4,4'-dimethyl-benzhydryl)-biphenyl

C₃₈H₂₄N₂O₂

2,7-Bis-(3,5-di-tert-butyl-benzylsulfanylmethyl)-biphenylene

Refernces

• 1、 Greszler, Stephen N.,Shelat, Bhadra,Voight, Eric A.. "Enabling Synthesis of ABBV-2222, A CFTR Corrector for the Treatment of Cystic Fibrosis". . p. 5725 - 5727. Retrieved 2019.
• 2、 Ahn, Jung-Mo,Wentworth Jr., Paul,Janda, Kim D. "Soluble polymer-supported convergent parallel library synthesis.". . p. 480 - 481. Retrieved 2003.
• 3、 Fu, Yue,Liu, Fang-Jie,Liu, Peng,Tang, Jian-Tao,Toste, F. Dean,Wu, Ting-Feng,Ye, Baihua,Zhang, Yue-Jiao. "Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides". supporting information. p. 1963 - 1974. Retrieved 2021/07/07.
• 4、 Appa, Rama Moorthy,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Venkateswarlu, Katta. "Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions". . . Retrieved 2021/01/11.