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512079

Sigma-Aldrich

Pentafluorophenyl isocyanate

97%

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5 ML
$708.00

$708.00

Estimated to ship onMay 17, 2025

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5 ML
$708.00

About This Item

Linear Formula:
C6F5NCO
CAS Number:
1591-95-3
Molecular Weight:
209.07
EC Number:
216-470-7
MDL number:
MFCD01863699
UNSPSC Code:
12352100
PubChem Substance ID:
24873607
NACRES:
NA.22

$708.00

Estimated to ship onMay 17, 2025

Request a Bulk Order

Quality Level

100

assay

97%

refractive index

n20/D 1.449 (lit.)

bp

52 °C/2 mmHg (lit.)

density

1.6 g/mL at 25 °C (lit.)

functional group

fluoro
isocyanate

storage temp.

2-8°C

SMILES string

Fc1c(F)c(F)c(N=C=O)c(F)c1F

InChI

1S/C7F5NO/c8-2-3(9)5(11)7(13-1-14)6(12)4(2)10

InChI key

QXLDBWRLZDBVGF-UHFFFAOYSA-N

Related Categories

General description

Pentafluorophenyl isocyanate (PFPI), an aryl isocyanate, is an N-protecting reagent.[1] The photoinduced intermolecular carbamoylation of tertiary ethereal C-H bond of fused bicyclic system using PFPI/benzophenone has been reported.[2] Reacting wood polymers with PFPI can make them resistant to fungal attack by forming a stable carbamate bond.[3]

Application

Pentafluorophenyl isocyanate may be used in the preparation of:
  • pentafluorophenyl end-capped poly(ethylene glycol) (PF-PEG-PF)[4]
  • 9-O-(pentafluorophenylcarbamoyl)quinine[5]
  • 9-O-(tert-butyldimethylsilyl)-10-(pentafluorophenylcarbamoyloxy)-6′-methoxy-11-norcinchonan-9-ol[5]
  • substituted 2,6-ethynylpyridine bisphenylurea scaffolds[6]
  • novel O-xylyl bridged hexaurea receptor for atmospheric CO2 uptake[7]

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW9998
MKCQ3653
MKCK6173
MKCK5848
MKCF5167

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Phenyl isocyanate

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Sigma-Aldrich

239690

Succinic anhydride

CO2-and O2-Sensitive Fluorophenyl End-Capped Poly (ethylene glycol).
Choi JY, et al.
Macromolecular Rapid Communications, 35(1), 66-70 (2014)
NMR enantiodiscrimination by pentafluorophenylcarbamoyl derivatives of quinine: C10 versus C9 derivatization.
Uccello-Barretta G, et al.
Chirality, 23(5), 417-417 (2011)
Fungal resistance of southern pine impregnated with methyl fluorophenyl carbamates or reacted with fluorophenyl isocyanates.
Chen GC, et al.
Wood and Fiber Science, 22(2), 165-172 (2007)
Jeffrey M Engle et al.
Chemical science, 3(4), 1105-1110 (2012-04-01)
A series of sixteen bisphenylureas based on a 2,6-bis(2-anilinoethynyl)pyridine scaffold have been synthesized for use as potential anion sensors. Prior work with one of these receptors revealed a distinct fluorescence response in the presence of a suitable anion source with
Elena Badaloni et al.
Journal of chromatography. A, 1217(7), 1024-1032 (2009-10-30)
The aim of the present study was to extend the use of the "Inverted Chirality Columns Approach (ICCA)" previously developed for the identification and quantitation of the trace enantiomer in highly enriched samples of the camptothecin (CPT) family of drugs
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