3459-92-5 Usage
Description
Dibenzyl carbonate (DBC) is a colorless low melting solid that is commonly used as a benzylating agent. It is formed through the transesterification of dimethyl carbonate and an excess of benzyl alcohol in the presence of CsF/α-Al2O3 (cesium fluoride/aluminum oxide).
Uses
1. Used in Chemical Synthesis:
Dibenzyl carbonate is used as an alkylating reagent for accelerating slow N-benzylation reactions. It is particularly effective in benzylating phenylacetonitrile, benzyl phenylacetate, and phenol.
2. Used in Pharmaceutical Industry:
Dibenzyl carbonate is used as a selective N,N-dibenzylation agent for primary aliphatic amines in the presence of phosphonium salts, which is crucial for the synthesis of various pharmaceutical compounds.
3. Used in Ionic Liquids:
Dibenzyl carbonate is utilized in ionic liquids to enhance the efficiency of N-benzylation reactions, making it a valuable component in the development of green and sustainable chemical processes.
Preparation
To a stirred solution of benzyl alcohol (0.216 g, 2.00 mol), tributylphosphine (0.303 g, 1.50 mmol), and CyTMG (0.394 g, 2.00 mmol) in DMF (2.00 mL), CO2 was added at room temperature. After 15 min, tetrabromomethane (0.663 g, 2.00 mmol) was added, the reaction vessel was sealed, and the contents were stirred for 2 h. Thereafter, the reaction mixture was diluted with ethyl acetate, washed successively with 0.5 m aqueous HCl and saturated aq. NaHCO3 solution, and dried over Na2SO4. Diphenylmetha- nol was added to the organic solution as an internal standard and the yield of dibenzyl carbonate was determined from the relative integrals of a methylene peak of the carbonate and a methine peak of diphenylmethanol in the 1H NMR spectrum of the ethyl acetate solution. Dibenzyl carbonate, prepared by a larger scale reaction of CO2 with benzyl alcohol (1.08 g, 10.0 mmol), was isolated by column chromatography (cyclohexane/ethyl acetate, 50:1) in 67.3% yield (0.816 g).
Check Digit Verification of cas no
The CAS Registry Mumber 3459-92-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,5 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3459-92:
(6*3)+(5*4)+(4*5)+(3*9)+(2*9)+(1*2)=105
105 % 10 = 5
So 3459-92-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O3/c16-15(17-11-13-7-3-1-4-8-13)18-12-14-9-5-2-6-10-14/h1-10H,11-12H2
3459-92-5Relevant articles and documents
Direct Synthesis of Alkyl 2-Alkynoates from Alk-1-ynes, CO2, and Bromoalkanes Catalysed by Copper(I) or Silver(I) Salt
Fukue, Yasuo,Oi, Shuichi,Inoue, Yoshio
, p. 2091 - 2092 (1994)
Alkyl alkynoates are synthesized directly from alk-1-ynes, CO2, and bromoalkanes in the presence of a catalytic amount of copper(I) or silver(I) salt.
Carbamate Synthesis Using a Shelf-Stable and Renewable C1 Reactant
Dobi, Zoltán,Reddy, B. Narendraprasad,Renders, Evelien,Van Raemdonck, Laurent,Mensch, Carl,De Smet, Gilles,Chen, Chen,Bheeter, Charles,Sergeyev, Sergey,Herrebout, Wouter A.,Maes, Bert U. W.
, p. 3103 - 3114 (2019/06/24)
4-Propylcatechol carbonate is a shelf-stable, renewable C1 reactant. It is easily prepared from renewable 4-propylcatechol (derived from wood) and dimethyl carbonate (derived from CO2) using a reactive distillation system. In this work, the 4-propylcatechol carbonate is used for the two-step synthesis of carbamates under mild reaction conditions. In the first step, 4-propylcatechol carbonate is treated with an alcohol at 50–80 °C in the presence of a Lewis acid catalyst, such as Zn(OAc)2?2 H2O. With liquid alcohols, no solvent is used and with solid alcohols 2-methyltetrahydrofuran is used as solvent. In the second step, the alkyl 2-hydroxy-propylphenyl carbonate intermediates obtained react with amines at room temperature in 2-methyltetrahydrofuran, forming the target carbamates and the byproduct 4-propylcatechol, which can be recycled into a carbonate reactant.
Carbon Dioxide Utilisation for the Synthesis of Unsymmetrical Dialkyl and Cyclic Carbonates Promoted by Basic Ionic Liquids
Goodrich, Peter,Gunaratne, H. Q. Nimal,Jin, Lili,Lei, Yuntao,Seddon, Kenneth R.
, p. 181 - 185 (2018/03/09)
An efficient and greener synthesis of unsymmetrical organic carbonates mediated by Hünig's base-appended basic ionic liquids, via carbon dioxide conversion, is described here. These ionic liquids were found to be effective bases for the fixation of carbon dioxide by various alcohols and benzyl bromide, at room temperature. When the alcohol and the halide functionalities are present within the same substrate, the reaction cleanly produces a cyclic carbonate. These functionalised basic ionic liquids were fully recyclable with no loss product yields.
