Dibenzyl terephthalate

Base Information

• Chemical Name: Dibenzyl terephthalate
• CAS No.: 19851-61-7
• Molecular Formula: C22H18O4
• Molecular Weight: 346.383
• Hs Code.: 2917399090
• European Community (EC) Number: 243-370-0
• DSSTox Substance ID: DTXSID80173600
• Nikkaji Number: J42.305J
• Wikidata: Q72463702
• Mol file: 19851-61-7.mol

Synonyms:Dibenzyl terephthalate;19851-61-7;dibenzyl benzene-1,4-dicarboxylate;1,4-Benzenedicarboxylic acid, 1,4-bis(phenylmethyl) ester;EINECS 243-370-0;1,4-Benzenedicarboxylic acid, bis(phenylmethyl) ester;SCHEMBL312287;terephthalic acid dibenzyl ester;DTXSID80173600;Terephthalic acid, dibenzyl ester;MFCD00075729;AS-80625;FT-0624659;E77573;W-110503

Chemical Property of Dibenzyl terephthalate

Chemical Property:

• Vapor Pressure: 3.96E-10mmHg at 25°C
• Melting Point: 95-97°C
• Refractive Index: 1.605
• Boiling Point: 500 °C at 760 mmHg
• Flash Point: 252.6 °C
• PSA: 52.60000
• Density: 1.208g/cm³
• LogP: 4.40060
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 346.12050905
• Heavy Atom Count: 26
• Complexity: 399

Purity/Quality:

99% ^*data from raw suppliers

DibenzylTerephthalate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=CC=C(C=C2)C(=O)OCC3=CC=CC=C3
• Uses: Dibenzyl terephthalate is used in the synthesis of Pharacine (P294550), which is a natural p-cyclophane from the bacterial strain Cytophaga sp. AM13.1. Pharacine is a poly(butylene terephthalate) dimer.

Technology Process of Dibenzyl terephthalate

There total 11 articles about Dibenzyl terephthalate 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%

benzyl methyl terephthalate (24318-74-9) + benzyl alcohol (100-51-6,185532-71-2) → p-dibenzyl benzenedicarboxylate (19851-61-7)

Guidance literature:

With lanthanum (III) nitrate * water; 1,1,1-trioctyl-1-methylphosphonium methylcarbonate; In hexane; for 5h; Molecular sieve; Reflux;

DOI:10.1039/c2cc34987f

Reference yield: 98.0%

terephthalic acid (100-21-0) + benzyl chloride (100-44-7) → p-dibenzyl benzenedicarboxylate (19851-61-7)

Guidance literature:

With triethylamine; for 2h; Heating; Inert atmosphere; Ionic liquid;

DOI:10.3906/kim-0904-39

Reference yield: 91.0%

terephthaloyl chloride (100-20-9) + benzyl alcohol (100-51-6,185532-71-2) → p-dibenzyl benzenedicarboxylate (19851-61-7)

Guidance literature:

In tetrahydrofuran; pyridine; Ambient temperature;

upstream raw materials:

terephthaloyl chloride

benzyl alcohol

1,4-benzenedicarboxylic acid dimethyl ester

terephthalic acid

Downstream raw materials:

C₄₆H₄₂O₁₂

butylene terephthalate cyclic trimer

Refernces

• 1、 Sun, Feixiang,Feng, Huangdi,Huang, Liliang,Huang, Junhai. "Ynoate-Initiated Selective C-N Esterification of Tertiary Amines under Transition-Metal and Oxidant-Free Conditions". supporting information. p. 713 - 717. Retrieved 2021/01/14.
• 2、 Mou, Fen,Sun, Yadong,Jin, Weiwei,Zhang, Yonghong,Wang, Bin,Liu, Zhiqing,Guo, Lei,Huang, Jianbin,Liu, Chenjiang. "Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions". . p. 23041 - 23045. Retrieved 2017/07/10.