19851-61-7

Basic information

• Product Name: DIBENZYL TEREPHTHALATE
• Synonyms: 1,4-Benzendicarboxylicacidbis(phenylmethyl)ester;TEREPHTHALIC ACID DIBENZYL ESTER;DIBENZYL TEREPHTHALATE;1,4-DIBENZYL TEREPHTHALATE;Benzyl Terephthalate;Einecs 243-370-0;Dibenzyl benzene-1,4-dicarboxylate
• CAS NO: 19851-61-7
• Molecular Formula: C₂₂H₁₈O₄
• Molecular Weight: 346.38
• EINECS: 243-370-0
• Product Categories: Aromatic Esters
• Mol File: 19851-61-7.mol

Chemical Properties

• Melting Point: 95-97°C
• Boiling Point: 441.12°C (rough estimate)
• Flash Point: 252.6 °C
• Appearance: /
• Density: 1.1637 (rough estimate)
• Vapor Pressure: 3.96E-10mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: DIBENZYL TEREPHTHALATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBENZYL TEREPHTHALATE(19851-61-7)
• EPA Substance Registry System: DIBENZYL TEREPHTHALATE(19851-61-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 19851-61-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Dibenzyl terephthalate is used as an intermediate in the synthesis of Pharacine (P294550), a natural p-cyclophane derived from the bacterial strain Cytophaga sp. AM13.1. Pharacine is a poly(butylene terephthalate) dimer, which has potential applications in the pharmaceutical industry due to its unique chemical properties and structure. The use of Dibenzyl terephthalate in this synthesis process allows for the creation of complex and valuable compounds with potential therapeutic applications.

InChI:InChI=1/C22H18O4/c23-21(25-15-17-7-3-1-4-8-17)19-11-13-20(14-12-19)22(24)26-16-18-9-5-2-6-10-18/h1-14H,15-16H2

Upstream product

• 100-39-0 benzyl bromide 
• 623-27-8 terephthalaldehyde, 
• 103-83-3 N,N'-dimethylbenzylamine 
• 100-21-0 terephthalic acid 
• 108-88-3 toluene 
• 24318-74-9 benzyl methyl terephthalate 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 10028-70-3 disodium terephthalate 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 100-20-9 terephthaloyl chloride 

Downstream Products

• 18520-63-3 monobenzyl terephthalate 
• 63440-94-8 butylene terephthalate cyclic trimer 
• 24968-12-5 C₄₆H₄₂O₁₂ 
• 1357620-18-8 N-(3-acetamido-5-(hydroxymethyl)phenyl)-N'-(3-(dimethylamino)propyl)-terephthalamide 
• 1357620-17-7 N-(3-acetamido-5-((tert-butyldimethylsilyloxy)methyl)phenyl)-N'-(3-(dimethylamino)propyl) terephthalamide 
• 1357620-14-4 benzyl 4-(3-morpholinopropylcarbamoyl)benzoate 
• 1357620-13-3 benzyl 4-(3-(diethylamino)propylcarbamoyl)benzoate 
• 1357620-12-2 benzyl 4-(3-(dimethylamino)propylcarbamoyl)benzoate 

Relevant articles and documents

Formation of gas-phase dianions and distonic ions as a general method for the synthesis of protected reactive intermediates. Energetics of 2,3- and 2,6-dehydronaphthalene

New methods for the regioselective formation of radical anions are described. Dicarboxylates are generated by electrospray ionization mass spectrometry and lose carbon dioxide and an electron upon collision-induced dissociation to afford distonic ions. These radical anions also can be synthesized via laser desorption, chemical ionization, and electron ionization of dibenzyl esters. Subsequent fragmentation of the remaining CO2 affords new radical anions corresponding to neutral reactive intermediates. By measuring the proton affinities and electron binding energies of these species, quantitative energetic information on carbenes, biradicals, and other transient molecules can be obtained. This approach is demonstrated by measuring the heats of formation of 2,3- and 2,6-dehydronaphthalene, ancillary thermochemical data also are derived, and the results are compared to either o- or p-benzyne.

Ynoate-Initiated Selective C-N Esterification of Tertiary Amines under Transition-Metal and Oxidant-Free Conditions

An efficient and selective method for metal-and oxidant-free deaminated esterification of tertiary amines is presented. In this protocol, ynoates play a key role to activate the Csp 3-N bond through a process of in situ generation of zwitterionic salts. The transformations show that Csp 3-N bond in the zwitterionic species has a lower dissociation energy than Csp 2-N bond, leading to break preferentially and be trapped by carboxylic acids to generate the corresponding products in moderate to good yield.

Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions

A metal-free protocol for the direct oxidative esterification of the Csp3-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.

Cyclic polybutylene terephthalate preparation

The invention specifically discloses a preparation method of novel cyclicpolybutylece terephthalate (PBT) dimer, wherein paraphthaloyl chloride and 1,4-butanediol are used as the raw materials for oriented synthesis of the cyclicpolybutylece terephthalate dimer through a protection and deprotectionstrategy, and the method is used for contrast analysis and detection of cyclicpolybutylece terephthalate dimer impurities in a PBT plastic. The chemical structural formula of the cyclicpolybutylece terephthalate dimer is described in the specification.

NOVEL SINGLE STEP ESTERIFICATION PROCESS OF ALDEHYDES USING A HETEROGENEOUS CATALYST

The present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using a heterogeneous catalyst with high yields. More particularly, the present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using Titanium superoxide with greater than 80% yields.

Polybutylene terephthalate cyclic trimerization preparation of (by machine translation)

The invention specifically has described a kind of new cyclic trimeric butylene terephthalate (Cyclic PBT Dimer) method for preparing, in the terephthalic chloride and 1, the 4 the protecting [...] butanediol as raw material with oriented synthesis strategy of deprotection of the polybutylene terephthalate cyclic trimerization, in the plastics can be used for the PBT polybutylene terephthalate cyclic trimerization contrast analysis of the impurity with the detection. Said product of this invention the chemical structural formula is: (by machine translation)

Mirror symmetry breaking in cubic phases and isotropic liquids driven by hydrogen bonding

Achiral supramolecular hydrogen bonded complexes between rod-like 4-(4-alkoxyphenylazo)pyridines and a taper shaped 4-substituted benzoic acid form achiral (Ia3d) and chiral “Im3m-type” bicontinuous cubic (I432) phases and a chiral isotropic liquid mesophase (Iso1[*]). The chiral phases, resulting from spontaneous mirror symmetry breaking, represent conglomerates of macroscopic chiral domains eventually leading to uniform chirality.

Titanium superoxide-a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant

Titanium superoxide efficiently catalysed the oxidative esterification of aldehydes with alkylarenes or alcohols, under truly heterogeneous conditions, to afford the corresponding benzyl and alkyl esters in excellent yields. Mechanistic studies have established that this "one pot" direct oxidative esterification process proceeds through a radical pathway, proven by a FTIR spectral study of a titanium superoxide-aldehyde complex as well as spin trapping experiments with TEMPO. The intramolecular version of this protocol has been successfully demonstrated in the concise synthesis of 3-butylphthalide, an anti-convulsant drug.

Electrogenerated N-heterocyclic carbene in ionic liquid: An insight into the mechanism of the oxidative esterification of aromatic aldehydes

An N-heterocyclic carbene (NHC), generated by cathodic reduction of BMIm BF4, mediates the oxidative esterification of aromatic aldehydes with organic bromides in the corresponding ionic liquid as solvent. The product recovery by simple extractive work-up with diethyl ether allowed the ionic liquid to be recycled up to 9 times for subsequent electrolyses, with no significant loss in the product yield. The isolation of an intermediate, whose structure was confirmed by synthesis and transformation into the ester, provided the key for a mechanistic insight into the reaction.

In situ generated "lanthanum(iii) nitrate alkoxide" as a highly active and nearly neutral transesterification catalyst

In situ generated lanthanum(iii) nitrate alkoxide is a highly active and nearly neutral transesterification catalyst, which can promote non-epimerized transesterification of α-substituted chiral carboxylic esters under reflux conditions.