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539899

Sigma-Aldrich

Bis(pentafluorophenyl) carbonate

97%

Synonym(s):
Pentafluorophenyl carbonate
Linear Formula:
(C6F5O)2CO
CAS Number:
Molecular Weight:
394.12
Beilstein:
2029727
MDL number:
PubChem Substance ID:

Quality Level

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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This Item
418080103799512079
Pentafluorophenol ReagentPlus®, ≥99%

Sigma-Aldrich

103799

Pentafluorophenol

mp

47-50 °C (lit.)

mp

47-50 °C (lit.)

mp

34-36 °C (lit.)

mp

-

reaction suitability

reaction type: Carbonylations

reaction suitability

-

reaction suitability

-

reaction suitability

-

application(s)

peptide synthesis

application(s)

-

application(s)

peptide synthesis

application(s)

-

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

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Customers Also Viewed

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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
Bis(pentafluorophenyl)carbonate
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2004)
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)
[Dipentafluorophenylcarbonate in the synthesis of oligonucleotides by the H-phosphonate method].
V A Efimov et al.
Bioorganicheskaia khimiia, 20(3), 323-326 (1994-03-01)

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