Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate

Base Information

• Chemical Name: Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate
• CAS No.: 55676-77-2
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• Hs Code.: 2917399090
• European Community (EC) Number: 259-749-9
• UNII: 48HJ27Q73L
• DSSTox Substance ID: DTXSID1069039
• Nikkaji Number: J21.983E
• Wikidata: Q81995830
• Mol file: 55676-77-2.mol

Synonyms:Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate;55676-77-2;methyl 2-(4-methoxycarbonylphenyl)benzoate;[1,1'-Biphenyl]-2,4'-dicarboxylic acid, dimethyl ester;Dimethyl (1,1'-biphenyl)-2,4'-dicarboxylate;EINECS 259-749-9;2,4'-dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate;(1,1'-Biphenyl)-2,4'-dicarboxylic acid, dimethyl ester;(1,1'-Biphenyl)-2,4'-dicarboxylic acid, 2,4'-dimethyl ester;[1,1'-Biphenyl]-2,4'-dicarboxylic acid, 2,4'-dimethyl ester;Dimethyl[1,1'-biphenyl]-2,4'-dicarboxylate;SCHEMBL68818;DTXSID1069039;48HJ27Q73L;Dimethyl 2,4'-biphenyldicarboxylate;MFCD06204222;AKOS016003142;DS-2393;2,4'-Biphenyldicarboxylic acid dimethyl ester;A870137;DIMETHYL [1,1-BIPHENYL]-2,4-DICARBOXYLATE;[1,1'-Biphenyl]-2,4'-dicarboxylicacid,2,4'-dimethyl ester

Chemical Property of Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate

Chemical Property:

• Boiling Point: 416.2 °C at 760 mmHg
• Flash Point: 210.4 °C
• PSA: 52.60000
• Density: 1.172 g/cm³
• LogP: 2.92680
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 344

Purity/Quality:

97% ^*data from raw suppliers

Dimethyl[1,1?-biphenyl]-2,4?-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C2=CC=CC=C2C(=O)OC

Technology Process of Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate

There total 14 articles about Dimethyl [1,1'-biphenyl]-2,4'-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 2-((N,N-dimethylsulfamoyl)oxy)benzoate → dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate (55676-77-2)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium phosphate; tricyclohexylphosphine; In tetrahydrofuran; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo202037x

Reference yield: 98.0%

methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate (905966-40-7) + methyl chlorobenzoate (610-96-8) → dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate (55676-77-2)

Guidance literature:

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

DOI:10.1055/s-0035-1562342

Reference yield: 96.0%

methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate (905966-40-7) + o-iodo-methyl-benzoic acid (610-97-9) → dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate (55676-77-2)

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:

o-iodo-methyl-benzoic acid

methyl 4-iodobenzoate

methanol

benzoic acid methyl ester

Refernces

• 1、 Malineni, Jagadeesh,Jezorek, Ryan L.,Zhang, Na,Percec, Virgil. "An Indefinitely Air-Stable σ-NiII Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates". supporting information. p. 2795 - 2807. Retrieved 2016/08/31.
• 2、 Leowanawat, Pawaret,Zhang, Na,Safi, Mehtap,Hoffman, David J.,Fryberger, Miriam C.,George, Aiswaria,Percec, Virgil. "Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature". experimental part. p. 2885 - 2892. Retrieved 2012/05/04.