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477907

Sigma-Aldrich

Dibenzyl carbonate

99%

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About This Item

Linear Formula:
(C6H5CH2O)2CO
CAS Number:
3459-92-5
Molecular Weight:
242.27
EC Number:
222-401-1
MDL number:
MFCD00014436
UNSPSC Code:
12352100
PubChem Substance ID:
24871426
NACRES:
NA.22

assay

99%

bp

180-190 °C/2 mmHg (lit.)

mp

29-33 °C (lit.)

SMILES string

O=C(OCc1ccccc1)OCc2ccccc2

InChI

1S/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

InChI key

PIZLBWGMERQCOC-UHFFFAOYSA-N

General description

Dibenzyl 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.

Application

Dibenzyl carbonate may be used in the synthesis of the following via benzylation reaction:
  • Benzyl phenyl ether from phenol.
  • 2,3-Diphenylpropionitrile from phenylacetonitrile.
  • Benzyl 2,3-diphenylpropionate from benzyl phenyl acetate.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV8035
BCBP5286V
BCBP0362V
BCBN1348V
BCBN0922V

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Selective N,N-dibenzylation of primary aliphatic amines with dibenzyl carbonate in the presence of phosphonium salts.
Loris A, et al.
The Journal of Organic Chemistry, 69(11), 3953-3956 (2004)
Selective mono-benzylation of methylene active compounds with dibenzyl carbonate: benzylation of phenol.
AlbertoaMarques C.
Journal of the Chemical Society. Perkin Transactions 1, 15, 1889-1893 (1995)
Synthesis of dibenzyl carbonate: towards a sustainable catalytic approach.
Fiorani G and Selva M.
Royal Society of Chemistry Advances, 4(4), 1929-1937 (2014)

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