355-38-4

Basic information

• Product Name: PERFLUOROHEXANOYL FLUORIDE 98
• Synonyms: PERFLUOROHEXANOYL FLUORIDE 98;Perfluorohexanoyl fluoride 98%;Hexanoyl fluoride,undecafluoro;Undecafluorohexanoyl fluoride;undecafluoro-Hexanoyl fluoride;Undecafluorohexanoic acid fluoride;2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl fluoride
• CAS NO: 355-38-4
• Molecular Formula: C₆F₁₂O
• Molecular Weight: 316.041
• EINECS: 206-582-4
• Mol File: 355-38-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 59 °C
• Flash Point: 18 °C
• Appearance: /
• Density: 1.66 g/cm³
• Vapor Pressure: 96.4mmHg at 25°C
• Refractive Index: 1.264
• CAS DataBase Reference: PERFLUOROHEXANOYL FLUORIDE 98(CAS DataBase Reference)
• NIST Chemistry Reference: PERFLUOROHEXANOYL FLUORIDE 98(355-38-4)
• EPA Substance Registry System: PERFLUOROHEXANOYL FLUORIDE 98(355-38-4)

Safety Data

• Hazard Codes: C
• Hazardous Substances Data: 355-38-4(Hazardous Substances Data)

Usage

General Description

PERFLUOROHEXANOYL FLUORIDE 98 is a chemical compound with the formula C6F13COF. It is a highly fluorinated organic compound that is commonly used as an intermediate in the production of various fluorochemicals and in the manufacturing of specialty polymers. It is a clear, colorless liquid with a strong, characteristic odor. PERFLUOROHEXANOYL FLUORIDE 98 is known for its high thermal stability, chemical inertness, and resistance to solvents, acids, and bases. It is used in a wide range of industrial applications, including as a raw material in the production of surfactants, pharmaceuticals, and agrochemicals. Additionally, it is used in the production of fluoropolymer additives and coatings for applications in electronics, aerospace, and automotive industries. However, it is important to handle PERFLUOROHEXANOYL FLUORIDE 98 with caution, as it is flammable and may cause skin and eye irritation.

InChI:InChI=1/C6F12O/c7-1(19)2(8,9)3(10,11)4(12,13)5(14,15)6(16,17)18

Synthetic route

2,2,3,3,4,4,5,5,6,6,6-Undecafluoro-hexanoic acid 1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-icosafluoro-1-trifluoromethyl-decyl ester (210972-72-8) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
at 182 - 224℃;	73%

7-oxabicyclo(2.2.1)heptane (279-49-2) → perfluoropentane (678-26-2) + perfluorohexanoyl fluoride (355-38-4) + perfluoro(2-ethyltetrahydrofuran) (356-48-9)

Conditions	Yield
With fluorine at -120 - 20℃; for 336h; Yields of byproduct given;	A n/a B n/a C 26.2%
With fluorine at -120 - 20℃; for 336h; Yield given;	A n/a B n/a C 26.2%

dihexyl ether (112-58-3) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With hydrogen fluoride anodische Fluorierung;

hexanoic acid (142-62-1) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With hydrogen fluoride anodische Fluorierung;

perfluoro-2-octene (65500-50-7) → trifluoroacetyl fluoride (354-34-7) + perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With ozone; trifluoroacetic acid at -18 - 0℃; Yield given. Yields of byproduct given;

Perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine (143813-73-4, 145733-85-3) → perfluorohexanoyl fluoride (355-38-4) + C6F13N

Conditions	Yield
With cesium fluoride at 100 - 110℃; for 12h; Yield given. Yields of byproduct given;

perfluoro-1-pentoxy-2-azaoct-1-ene → perfluorohexanoyl fluoride (355-38-4) + C6F13N

Conditions	Yield
With cesium fluoride at 100℃; for 12h; Yield given. Yields of byproduct given;

(E)-perfluorooct-2-ene (31143-13-2) + trifluoroacetic acid (76-05-1) → perfluorohexanoyl fluoride (355-38-4) + trifluoroacetyl peroxide (359-48-8)

Conditions	Yield
With oxygen; ozone at 0℃; Rate constant; var. reaction conditions; also in the presence of SbF5 and HClO4;

cyclohexanol (108-93-0) → perfluoropentane (678-26-2) + perfluorohexanoyl fluoride (355-38-4) + perfluorocyclohexane (355-68-0)

Conditions	Yield
With fluorine -120 deg C to r.t.; Yields of byproduct given;	A 1.2 g B n/a C n/a
With fluorine -120 deg C to r.t.; Yield given;	A 1.2 g B n/a C n/a

trans-3,5-difluoro-5-perfluoropentyl-3-trifluoromethyl-1,2,4-trioxolane + cis-3,5-difluoro-5-perfluoropentyl-3-trifluoromethyl-1,2,4-trioxolane → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Ring cleavage; Heating;

perfluoro-2-octene (65500-50-7) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: O3; O2 / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 2 h / 15 - 20 °C 2: Heating View Scheme

Perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine (143813-73-4, 145733-85-3) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 150 - 170 °C 2: CsF / 12 h / 100 °C View Scheme

n-perfluorohexyl iodide (355-43-1) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
With phosphorus pentachloride; sulfuric acid at 20 - 70℃; for 17.5h;	58.7 %Chromat.

mercury(II) fluoride + perfluorohexanoyl cyanide dimer → perfluorohexanoyl fluoride (355-38-4)

perfluorohexanoyl cyanide dimer + silver fluoride → perfluorohexanoyl fluoride (355-38-4)

hexanoyl fluoride (372-80-5) → perfluorohexanoyl fluoride (355-38-4)

Conditions	Yield
Electrochemical reaction;

perfluorohexanoyl fluoride (355-38-4) + p-phenylbenzyl bromide (2567-29-5) → C19H11F13O

Conditions	Yield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 12h; Temperature; Reagent/catalyst; Inert atmosphere;	78%

perfluorohexanoyl fluoride (355-38-4) + allyl bromide (106-95-6) → C9H5F13O

Conditions	Yield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;	75%

perfluorohexanoyl fluoride (355-38-4) + ethyl iodide (75-03-6) → C8H5F13O

Conditions	Yield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;	30%

methanol (67-56-1) + perfluorohexanoyl fluoride (355-38-4) → perfluorohexanoic acid methyl ester (424-18-0)

perfluorohexanoyl fluoride (355-38-4) → undecafluoro-hexanoic acid amide (335-54-6)

Conditions	Yield
With ammonia

Hexafluoropropene oxide (428-59-1) + perfluorohexanoyl fluoride (355-38-4) → F(CF2)6OCF(CF3)COF (13140-31-3)

Conditions	Yield
With Tetraethylene glycol dimethyl ether; cesium fluoride at 0 - 20℃; under 0 Torr;	79.6 %Chromat.

Upstream product

• 112-58-3 dihexyl ether 
• 142-62-1 hexanoic acid 
• 65500-50-7 perfluoro-2-octene 
• 31143-13-2 (E)-perfluorooct-2-ene 
• 76-05-1 trifluoroacetic acid 
• 372-80-5 hexanoyl fluoride 
• 11113-87-4 silver fluoride 
• 7783-39-3 mercury(II) fluoride 
• 355-43-1 n-perfluorohexyl iodide 
• 143813-73-4 Perfluoro-cis-2-n-hexyl-3-n-pentyloxaziridine 
• 210972-72-8 2,2,3,3,4,4,5,5,6,6,6-Undecafluoro-hexanoic acid 1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-icosafluoro-1-trifluoromethyl-decyl ester 
• 108-93-0 cyclohexanol 
• 279-49-2 7-oxabicyclo(2.2.1)heptane 

Downstream Products

• 335-54-6 Perfluorhexanamid 
• 424-18-0 perfluorohexanoic acid methyl ester 

Relevant articles and documents

Homogeneous catalytic hydrogenation of perfluoro methyl esters

The first example of perfluoroalkyl methyl ester RfC(O)OMe (Rf = C3F7, C5F11) reduction by homogeneous catalytic hydrogenation with the ruthenium catalyst Ru-MACHO is herein reported. The hydrogenation process leads to the corresponding perfluorinated alcohols thus replacing sodium borohydride that has so far represented the state of art in perfluoro ester reduction.

Ozonides of perfluorooct-1-ene and perfluorooct-2-ene

Ozonides of higher perfluoroalkenes were prepared for the first time by ozonation of perfluorooct-1-and -2-enes in Freon-113. The structures of the resulting compounds were confirmed by 13C NMR spectroscopy and GLC-mass spectrometry.

Some Novel Reactions of Perfluoro-2,3-dialkyloxaziridines

Perfluoro-2,3-dialkyloxaziridines rearrange at 120-160 deg C into RfN=CF-OR'f quantitatively.Reaction with SbF5 at elevated temperature leads to the formation of the isomeric alkoxy imines RfON=CFR'f.Reaction with CsF in the absence of a solvent results in formation of a mixture of the corresponding acyl fluoride R'fC(O)F and N-fluoro imine R'fCF=NF.In contrast, reaction between perfluoro-2-butyl-3-propyloxaziridine and CsF in MeCN produces C4F9ON=CFC3F7.Interaction of this oxaziridine with polyfluoro ketones and COF2 in the presence of CsF in polar solvents leads to the formation of alkoxy imines R''fON=CFC3F7.