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539899

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/REAXYS Number:
2029727
MDL number:
MFCD00368353
UNSPSC Code:
12352101
PubChem Substance ID:
24878273
NACRES:
NA.22

Product Name

Bis(pentafluorophenyl) carbonate, 97%

Quality Level

200

assay

97%

reaction suitability

reaction type: Carbonylations

mp

47-50 °C (lit.)

application(s)

peptide synthesis

functional group

carbonate
fluoro

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0459
BCCM4031
BCCK1848
BCCH0277
BCCH6393

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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)
[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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