66249-23-8

Basic information

• Product Name: Benzene, (3,3,4,4,5,5,6,6,6-nonafluoro-1-hexynyl)-
• CAS NO: 66249-23-8
• Molecular Formula: C12H5F9
• Molecular Weight: 320.157
• Mol File: 66249-23-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, (3,3,4,4,5,5,6,6,6-nonafluoro-1-hexynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (3,3,4,4,5,5,6,6,6-nonafluoro-1-hexynyl)-(66249-23-8)
• EPA Substance Registry System: Benzene, (3,3,4,4,5,5,6,6,6-nonafluoro-1-hexynyl)-(66249-23-8)

Safety Data

• Hazardous Substances Data: 66249-23-8(Hazardous Substances Data)

Upstream product

• 423-39-2 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane 
• 536-74-3 phenylacetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 754-34-7 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane 
• 57947-31-6 2-phenylethenyl(triphenylphosphine)gold(I) 

Downstream Products

• 54864-78-7 3-perfluoropropyl-5-phenyl-1H-pyrazole 

Relevant articles and documents

Photoinitiated Reactions of Haloperfluorocarbons with Gold(I) Organometallic Complexes: Perfluoroalkyl Gold(I) and Gold(III) Complexes

The study of perfluoroalkyl metal complexes is key to understand and improve metal-promoted perfluoroalkylation reactions. Herein, we report the synthesis of the first gold complexes with primary or secondary perfluoroalkyl ligands by photoinitiated reactions between AuI organometallic complexes and iodoperfluoroalkanes. Complexes of the types LAuRF (L=PPh3 or N,N-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; RF=n-C4F9, n-C6F13, i-C3F7, c-C6F11) and [Au(RF)(Ar)I(PPh3)] (Ar=2,4,6-trimethylphenyl) have been isolated and characterized. Alkynes RFC≡CR were formed by reaction of Ph3PAuC≡CR (R=Ph, nHex) with IRF (RF=n-C4F9, i-C3F7). According to the evidences obtained, this transformation undergoes through a photoinitiated radical mechanism. AuIII complexes [Au(n-C4F9)(X)(Y)L] (X=Y=Cl, Br, I, Me; X=Me, Y=I) have been prepared or in situ generated, and their thermal or photochemical decomposition reactions have been studied.

Copper-Catalyzed Perfluoroalkylation of Alkynyl Bromides and Terminal Alkynes

A copper-catalyzed one-pot perfluoroalkylation of alkynyl bromides and terminal alkynes has been disclosed, and the corresponding perfluoroalkylated alkynes could be attained in good to excellent yields. The new straightforward transformation shows high efficiency (0.01-0.5 mol % catalyst loading), broad substrate scope, and remarkable functional group tolerance and provides a facile approach for useful application in life and material sciences.

Silver-Mediated Perfluoroalkylation of Terminal Alkynes with Perfluoroalkyl Iodides

The incorporation of a perfluoroalkyl group (RF) into drug candidates has become an increasingly important strategy in drug molecule design. In this study, the silver-mediated perfluoroalkylation reaction based on the addition-elimination process of terminal alkynes which was initiated by a perfluoroalkyl radical to form a C(sp)-RF bond has been developed. The reaction proceeds under mild conditions using readily available, low-cost perfluoroalkyl iodides as the sources of the RF group. This method allows access to a variety of perfluoroalkylated alkynes.