754-85-8

Basic information

• Product Name: 1H,1H,1H-PENTADECAFLUORO-2-NONANONE
• Synonyms: 1H,1H,1H-PERFLUORO-2-NONANONE;1H,1H,1H-PENTADECAFLUORO-2-NONANONE;METHYL PENTADECAFLUOROHEPTYL KETONE;METHYL PERFLUOROHEPTYL KETONE;Methyl Perfluoroheptyl Ketone 1H,1H,1H-Pentadecafluoro-2-nonanone 1H,1H,1H-Perfluoro-2-nonanone 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-Pentadecafluoro-2-nonanone
• CAS NO: 754-85-8
• Molecular Formula: C₉H₃F₁₅O
• Molecular Weight: 412.1
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 754-85-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 57 °C
• Flash Point: 51.4°C
• Appearance: /
• Density: 1.69
• Vapor Pressure: 4.31mmHg at 25°C
• Refractive Index: 1.3000 to 1.3040
• CAS DataBase Reference: 1H,1H,1H-PENTADECAFLUORO-2-NONANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H,1H-PENTADECAFLUORO-2-NONANONE(754-85-8)
• EPA Substance Registry System: 1H,1H,1H-PENTADECAFLUORO-2-NONANONE(754-85-8)

Safety Data

• RIDADR: UN 1224 3/PG II
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 754-85-8(Hazardous Substances Data)

Usage

General Description

1H,1H,1H-PENTADECAFLUORO-2-NONANONE, also known as perfluorononan-2-one, is a synthetic chemical compound belonging to the class of fluoroorganic compounds. It is a colorless liquid with a strong, sweet odor and is insoluble in water but miscible in organic solvents. 1H,1H,1H-PENTADECAFLUORO-2-NONANONE is commonly used as a solvent in organic synthesis, as well as a precursor for the production of various other fluorinated compounds. It is also used in the manufacturing of pharmaceuticals and agrochemicals. Its unique chemical properties and stability make it a valuable compound in a wide range of industrial applications. However, it is important to handle this chemical with care due to its potential health hazards.

InChI:InChI=1/C9H3F15O/c1-2(25)3(10,11)4(12,13)5(14,15)6(16,17)7(18,19)8(20,21)9(22,23)24/h1H3

Upstream product

• 335-67-1 Perfluorooctanoic acid 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 36554-97-9 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,11,11,12,12,13,13,14,14,15,15,16,16,17,17,17-triacontafluoroheptadecan-8,10-dione 
• 75823-99-3 di F-heptyl-3,5 hydroxy-5 phenyl-1 Δ² pyrazoline 
• 75823-89-1 3,5-Bis-pentadecafluoroheptyl-1-phenyl-1H-pyrazole 

Relevant articles and documents

SYNTHESIS OF THE CYANOHYDRIN OF METHYL PERFLUOROHEPTYL KETONE AND REACTION OF THE KETONE WITH HYDROGEN CYANIDE

The cyanohydrin of methyl perfluoroheptyl ketone 2 was able to be synthesized by a two-step process, i.e., an addition of sodium bisulfite and subsequent treatment with sodium cyanide.When equimolar amounts of ketone 2 and sodium cyanide were reacted in water or dipolar aprotic solvent such as dimethylformamide, acetonitrile, 1,2-dimethoxyethane and tetrahydrofuran, cyclic addition products composed of two molecules of ketone 2 and one molecule of hydrogen cyanide were exclusively formed as 2,5-dimethyl-2,5-bis(perfluoroheptyl)-4-oxazolidone 6 and 2,5-dimethyl-2,5-bis(per fluoroheptyl)-1,3-dioxolane-4-one 7 instead of the cyanohydrin of ketone 2.It is conceivable that a solubility characteristic of a compound carrying a long perfluoroalkyl group is responsible for the exclusive formation of cyclic compounds 6 and 7.

An efficient, overall [4+1] cycloadditon of 1,3-dienes and nitrene precursors

Intermolecular cycloadditions of conjugated dienes and nitrene precursors usually produce aziridines. A generally useful method was lacking to directly provide the [4+1] cycloadducts, 3-pyrrolines. We have realized this transformation by using an uniquely active catalyst, copper(II) 1,1,1,5,5,5-hexafluoroacetylacetonate ([Cu(hfacac)2]). The method is applicable to a wide array of dienes with good yields. When 1,4-disubsituted dienes are used as substrates, good-to-excellent cis or trans selectivity can be obtained. Interestingly, the cis or trans preference depends on the nature of the substituents, rather than diene geometry. Mechanistic studies reveal that the [4+1] cycloaddition proceeds through diene aziridination and subsequent ring expansion. Among common copper catalysts, only [Cu(hfacac)2] can efficiently catalyze both steps, which explains the unique efficiency of the catalyst.

Wacker oxidation of alkenes using a fluorous biphasic system. A mild preparation of polyfunctional ketones

Various alkenes are oxidized to the corresponding ketones using t-BuOOH in the presence of a palladium(II) catalyst bearing perfluorinated ligands using a biphasic solvent system of benzene and bromoperfluorooctane.