1591-95-3

Basic information

• Product Name: PENTAFLUOROPHENYL ISOCYANATE 97
• Synonyms: PENTAFLUOROPHENYL ISOCYANATE 97;Isocyanate, pentafluorophenyl-;perfluorophenyl isocyanate;1,2,3,4,5-pentafluoro-6-isocyanatobenzene;Pentafluorophenyl isocyanate 97%;2,3,4,5,6-PentafluoroPhenyl isocyanate;Pentafluoroisocyanatobenzene
• CAS NO: 1591-95-3
• Molecular Formula: C₇F₅NO
• Molecular Weight: 209.073016
• EINECS: 216-470-7
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 1591-95-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 36 °C
• Boiling Point: 52 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.6 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.349mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: PENTAFLUOROPHENYL ISOCYANATE 97(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROPHENYL ISOCYANATE 97(1591-95-3)
• EPA Substance Registry System: PENTAFLUOROPHENYL ISOCYANATE 97(1591-95-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 23-26-36
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 1591-95-3(Hazardous Substances Data)

Usage

Description

Pentafluorophenyl isocyanate (PFPI), an aryl isocyanate, is an N-protecting reagent known for its versatile applications in various industries. It is characterized by its ability to form stable carbamate bonds and has been reported to exhibit photoinduced intermolecular carbamoylation of tertiary ethereal C-H bonds in fused bicyclic systems.

Uses

Used in Pharmaceutical Industry:
Pentafluorophenyl isocyanate is used as a reactant for the inhibition of carbonic anhydrase IX and antimetastatic activity in breast cancer metastasis of ureidobenzenesulfonamides. This application is significant as it contributes to the development of potential treatments for breast cancer and its metastasis.
Used in Wood Industry:
In the wood industry, PFPI is used to make wood polymers resistant to fungal attack. The reaction between wood polymers and PFPI forms a stable carbamate bond, which enhances the durability and resistance of the wood material against fungal degradation.
General Description:
Pentafluorophenyl isocyanate (PFPI) is a versatile aryl isocyanate that serves as an N-protecting reagent in various applications. Its ability to form stable carbamate bonds and participate in photoinduced intermolecular carbamoylation reactions makes it a valuable compound in the pharmaceutical and wood industries.

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

Upstream product

• 124-38-9 carbon dioxide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 58751-08-9 2,3,4,5,6-pentafluoroformanilide 
• 75-44-5 phosgene 
• 58751-09-0 2,3,4,5,6-pentafluorophenyl isocyanide 
• 80684-62-4 F-benzohydroxamic acid 
• 2251-50-5 pentafluorobenzoylchloride 
• 201230-82-2 carbon monoxide 
• 1423-15-0 perfluorophenyl azide 

Downstream Products

• 1061377-18-1 1-(3-(3-morpholinopropoxy)phenyl)-3-(perfluorophenyl)urea 
• 1315572-62-3 N-methoxy-N'-(pentafluorophenyl)urea 
• 953090-17-0 C₁₁H₈F₅N₂O₄P 
• 953089-98-0 C₁₄H₉F₁₁NO₆P 
• 36375-78-7 pentafluorophenyl nitrene 

Relevant articles and documents

Reactions of a cerium(III) amide with heteroallenes: Insertion, silyl-migration and de-insertion

Reactions of Ce[N(SiMe3)PhF]3 (-PhF = pentafluorophenyl) toward small molecules of the type E1CE2 (E1, E2 = O, S, NR), including carbon disulfide, carbodiimide, carbon dioxide, isocyanate and isothiocyanate are reported, resulting in distinct products, including cerium(iii) dithiocarbamate, cerium(iii) guanidinate, isocyanates and unsymmetric carbodiimides. These reactions were rationalized as three consecutive stages of the same reaction pathway: insertion, silyl-migration and de-insertion.

Specific inhibitors of puromycin-sensitive aminopeptidase with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton

Specific puromycin-sensitive aminopeptidase (PSA) inhibitors with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton were prepared and their structure-activity relationships were investigated. The nature (F, Cl or Br), number and position(s) of the halogen atom(s) introduced into the 3-phenyl group were concluded to be critical determinants of the inhibitory activity.

N-(POLYFLUOROARYL)-HIDROXYLAMINES. SYNTHESIS AND PROPERTIES

Fluorine-containing N-arylhydroxylamines have been obtained by the reaction of hydroxylamine or its N- and O-derivatives on polyfluorinated benzenes and pentafluoropyridine.The influence of fluorine atoms on the reactivity of hydroxylamino group has been investigated.The reaction of N-polyflouroarylhydroxylamines with aldehydes has been shown not to occur, whereas their reaction with nitrosobenzenes leads to azoxybenzenes and with Lewis acids leads to corresponding nitrosobenzenes, azoxybenzenes and anilines.The action of acids on 2,3,5,6-tetrafluorophenylhydroxylamine leads to the acid-catalyzed rearrangement of the latter into 4-amino-2,3,5,6-tetrafluorophenol.C,N-Diarylnitrones have been obtained by the oxidation with MnO2 of fluorine-containing arylhydroxylamines possessing the CH-fragment in an α-position.