Dimethyl 5-phenylisophthalate

Base Information

• Chemical Name: Dimethyl 5-phenylisophthalate
• CAS No.: 21991-00-4
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.285
• Hs Code.: 2917399090
• European Community (EC) Number: 621-848-3
• DSSTox Substance ID: DTXSID30401607
• Nikkaji Number: J1.490.731I
• Mol file: 21991-00-4.mol

Synonyms:21991-00-4;dimethyl 5-phenylisophthalate;Dimethyl 5-phenylbenzene-1,3-dicarboxylate;dimethyl biphenyl-3,5-dicarboxylate;Dimethyl [1,1'-biphenyl]-3,5-dicarboxylate;[1,1'-Biphenyl]3,5-dicarboxylic acid demethyl ester;[1,1'-Biphenyl] 3,5-dicarboxylic acid demethyl ester;SCHEMBL7823750;DTXSID30401607;GVLNGQSSXSIUGH-UHFFFAOYSA-N;AKOS005266189;AC-12341;I11743;J-014397;BIPHENYL-3,5-DICARBOXYLIC ACID DIMETHYL ESTER

Chemical Property of Dimethyl 5-phenylisophthalate

Chemical Property:

• Vapor Pressure: 2.18E-07mmHg at 25°C
• Refractive Index: 1.558
• Boiling Point: 423.8°Cat760mmHg
• Flash Point: 215.1°C
• PSA: 52.60000
• Density: 1.172g/cm³
• LogP: 2.92680
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 322

Purity/Quality:

99%min ^*data from raw suppliers

BIPHENYL-3,5-DICARBOXYLIC ACID DIMETHYL ESTER Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dimethyl 5-phenylisophthalate

There total 13 articles about Dimethyl 5-phenylisophthalate 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: 82.0%

dimethyl 5-bromoisophthalate (51760-21-5) + phenylboronic acid (98-80-6) → 1,3-dimethyl 5-phenylbenzene-1,3-dicarboxylate (21991-00-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In ethanol; water; toluene; at 100 ℃; for 6h;

Reference yield: 78.0%

dimethyl 5-(pinacolboryl)isophthalate (944392-68-1) + bromobenzene (108-86-1,52753-63-6) → 1,3-dimethyl 5-phenylbenzene-1,3-dicarboxylate (21991-00-4)

Guidance literature:

dimethyl 5-(pinacolboryl)isophthalate; bromobenzene; With potassium carbonate; In 1,4-dioxane; at 20 ℃; for 0.5h;

With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 65 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.inorgchem.5b01623

Reference yield: 57.0%

5-iodo-isophthalic acid dimethyl ester (51839-15-7) + phenylboronic acid (98-80-6) → 1,3-dimethyl 5-phenylbenzene-1,3-dicarboxylate (21991-00-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In diethyl ether; water; toluene; for 6h; Schlenk technique; Glovebox; Inert atmosphere; Heating;

DOI:10.1021/acs.joc.0c01950

upstream raw materials:

dimethyl 5-bromoisophthalate

phenylboronic acid

dimethyl 5-aminoisophthalate

benzene

Downstream raw materials:

biphenyl-3,5-dicarboxylic acid 5-({(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]propyl}amide) 3-dipropylamide

3,5-Bis-di-(biphenyl-4-yl)-brommethyl-biphenyl

1,1-dimethylethyl (2S,5S)-5-<<5-<(diethoxyphosphoryl)methyl><1,1'-biphenyl>-3-yl>methyl>-2-(1,1-dimethylethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate

1,1-dimethylethyl (2R,5R)-5-<<5-<(diethoxyphosphoryl)methyl><1,1'-biphenyl>-3-yl>methyl>-2-(1,1-dimethylethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate

Refernces

• 1、 Gao, Pengcheng,Szostak, Michal. "Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation". supporting information. p. 6010 - 6015. Retrieved 2020/07/30.
• 2、 Qiu, Li,McCaffrey, Ryan,Jin, Yinghua,Gong, Yu,Hu, Yiming,Sun, Hongliang,Park, Wounjhang,Zhang, Wei. "Cage-templated synthesis of highly stable palladium nanoparticles and their catalytic activities in Suzuki-Miyaura coupling". . p. 676 - 680. Retrieved 2018/01/28.