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512079

Sigma-Aldrich

Pentafluorophenyl isocyanate

97%

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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

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.)

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. The photoinduced intermolecular carbamoylation of tertiary ethereal C-H bond of fused bicyclic system using PFPI/benzophenone has been reported. Reacting wood polymers with PFPI can make them resistant to fungal attack by forming a stable carbamate bond.

Application

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

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 Code

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

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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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)
Avijit Pramanik et al.
Organic letters, 16(2), 366-369 (2013-12-20)
A new hexaurea receptor has been synthesized, which absorbs atmospheric CO2 to produce an air-stable solid carbonate complex under normal conditions. Structural analysis of the carbonate complex with this receptor suggests that the carbonate is fully encapsulated within its highly
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
Photoinduced carbamoylation of ethereal C-H bonds using pentafluorophenyl isocyanate.
Kamijo S, et al.
Tetrahedron Letters, 52(22), 2885-2888 (2011)
NMR enantiodiscrimination by pentafluorophenylcarbamoyl derivatives of quinine: C10 versus C9 derivatization.
Uccello-Barretta G, et al.
Chirality, 23(5), 417-417 (2011)
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