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Sigma-Aldrich

Bis(pentafluorophenyl) carbonate

97%, for peptide synthesis

Synonym(s):

Pentafluorophenyl carbonate

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About This Item

Linear Formula:
(C6F5O)2CO
CAS Number:
59483-84-0
Molecular Weight:
394.12
Beilstein:
2029727
MDL number:
MFCD00368353
UNSPSC Code:
12352101
PubChem Substance ID:
24878273
NACRES:
NA.22

product name

Bis(pentafluorophenyl) carbonate, 97%

Assay

97%

reaction suitability

reaction type: Carbonylations

mp

47-50 °C (lit.)

application(s)

peptide synthesis

SMILES string

Fc1c(F)c(F)c(OC(=O)Oc2c(F)c(F)c(F)c(F)c2F)c(F)c1F

InChI

1S/C13F10O3/c14-1-3(16)7(20)11(8(21)4(1)17)25-13(24)26-12-9(22)5(18)2(15)6(19)10(12)23

InChI key

IOVVFSGCNWQFQT-UHFFFAOYSA-N

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General description

Bis(pentafluorophenyl) carbonate is the equivalent of carbonyl compound generally used in coupling reactions. It is used as a reagent in the preparation of azapeptides.

Application

Bis(pentafluorophenyl) carbonate can be used in the preparation of:
  • A cyclic carbonate named 6,6′-(ethane-1,2-diyl)bis(1,3,6-dioxazocan-2-one), which is a key intermediate for the synthesis of non-isocyanate polyurethanes.
  • A coumarin based aliphatic polycarbonate named 5-(4-methylumbelliferyloxycarbonyl)-5-methyl-1,3-dioxan-2-one (MUC).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bis(pentafluorophenyl)carbonate
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2004)
V N Medvedkin et al.
Bioorganicheskaia khimiia, 15(4), 460-464 (1989-04-01)
Dipentafluorophenylcarbonate, belonging to transesterifiying reagents, has been prepared and used for the synthesis of pentafluorophenyl esters of amino acids. In contrast to many other reagents of the kind, its preparation is simple, it is highly reactive and at the same
Synthesis of cinnamoyl and coumarin functionalized aliphatic polycarbonates
Chesterman JP, et al.
Polym. Chem., 8(48), 7515-7528 (2017)
Room temperature synthesis of non-isocyanate polyurethanes (NIPUs) using highly reactive N-substituted 8-membered cyclic carbonates
Yuen A, et al.
Polym. Chem., 7(11), 2105-2111 (2016)
V A Efimov et al.
Nucleic acids research, 21(23), 5337-5344 (1993-11-25)
Dipentafluorophenyl carbonate has been successfully used as condensing agent for the internucleotide bond formation in the synthesis of oligonucleotides via H-phosphonate approach. The mechanism of a nucleotide component activation with this reagent has been investigated with the help of 31P
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