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DIBENZYL CARBONATE

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CAS:3459-92-5
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DIBENZYL CARBONATE Basic information
Product Name:DIBENZYL CARBONATE
Synonyms:Carbonic acid, bis(phenylmethyl) ester;CARBONIC ACID DIBENZYL ESTER;DIBENZYL CARBONATE;Dibenzylcarbonate,98%;dibenzyl carbazate;NSC 406789;Dibenzyl carbonate 99%;Linezolid Impurity 50
CAS:3459-92-5
MF:C15H14O3
MW:242.27
EINECS:222-401-1
Product Categories:Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Carbonates;Carbonyl Compounds;Organic Building Blocks
Mol File:3459-92-5.mol
DIBENZYL CARBONATE Structure
DIBENZYL CARBONATE Chemical Properties
Melting point 29-33 °C(lit.)
Boiling point 180-190 °C2 mm Hg(lit.)
density 1.1515 (rough estimate)
refractive index 1.5485
Fp >230 °F
solubility Sparingly Soluble (0.099 g/L) (25°C).
form powder to lump
color White to Almost white
Sensitive Air Sensitive
BRN 1882864
CAS DataBase Reference3459-92-5(CAS DataBase Reference)
EPA Substance Registry SystemCarbonic acid, bis(phenylmethyl) ester (3459-92-5)
Safety Information
Hazard Codes Xn
Risk Statements 21/22
Safety Statements 36
WGK Germany 3
TSCA Yes
HS Code 29209090
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
DIBENZYL CARBONATE Usage And Synthesis
Chemical PropertiesColorless low melting solid
UsesIonic liquids can effectively accelerate slow N-benzylation reactions utilizing dibenzyl carbonate as an alkylating reagent. Dibenzyl carbonate (DBzlC) has been used to benzylate phenylacetonitrile, benzyl phenylacetate and phenol. Selective N, N-dibenzylation of primary aliphatic amines was carried with dibenzyl carbonate in the presence of phosphonium salts.
PreparationTo 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).
Synthesis Reference(s)The Journal of Organic Chemistry, 60, p. 6205, 1995 DOI: 10.1021/jo00124a044
General DescriptionDibenzyl carbonate (DBC) is commonly used as a benzylating agent. Dimethyl carbonate and excess of benzyl alcohol undergoes transesterification in the presence of CsF/α-Al2O3 (cesium fluoride/aluminum oxide) to form DBC. The formation of N,N-dibenzyl derivatives by the reaction of primary aliphatic amines with DBC in the presence of phosphonium salts has been investigated.
DIBENZYL CARBONATE Preparation Products And Raw materials
Preparation ProductsBenzyltrimethylammonium bromide-->N-CARBOBENZOXY-1,3-DIAMINOPROPANE HYDROCHLORIDE
Tag:DIBENZYL CARBONATE(3459-92-5) Related Product Information
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