376-27-2

Basic information

• Product Name: METHYL PERFLUOROOCTANOATE
• Synonyms: METHYL PERFLUOROOCTANOATE;METHYL PENTADECAFLUOROOCTANOATE;PENTADECAFLUOROOCTANOIC ACID METHYL ESTER;PERFLUOROOCTANOIC ACID METHYL ESTER;Methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate;Octanoic acid, perfluoro-, methyl ester;pentadecafluoro-octanoicacimethylester;methyl pentadecafluorooctanotate
• CAS NO: 376-27-2
• Molecular Formula: C₉H₃F₁₅O₂
• Molecular Weight: 428.09
• EINECS: 206-808-1
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 376-27-2.mol

Chemical Properties

• Boiling Point: 159-160 °C(lit.)
• Flash Point: 150 °F
• Appearance: clear colorless liquid
• Density: 1.786 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.68mmHg at 25°C
• Refractive Index: n20/D 1.305(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1809817
• CAS DataBase Reference: METHYL PERFLUOROOCTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL PERFLUOROOCTANOATE(376-27-2)
• EPA Substance Registry System: METHYL PERFLUOROOCTANOATE(376-27-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 36/37/38
• Safety Statements: 24/25-26
• WGK Germany: 3
• RTECS: RH0783200
• TSCA: T
• HazardClass: FLAMMABLE
• Hazardous Substances Data: 376-27-2(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
METHYL PERFLUOROOCTANOATE is used as a precursor for the synthesis of monodisperse perfluoroalkyl N-polyethoxylated amides, which are potential nonionic fluorinated surfactants.
2. Used in Solubility Studies:
METHYL PERFLUOROOCTANOATE is used as a component in investigating the mutual solubility curves of fluorocarbon-hydrocarbon systems.
3. Used in Polymer Science:
METHYL PERFLUOROOCTANOATE is used as a starting material for the synthesis of fluorine-containing monomers, such as N-(5-hydroxypent-1-yl)perfluorooctaneamide.
4. Used in Nanotechnology:
METHYL PERFLUOROOCTANOATE is used in the preparation of 2-chloro-1,1-dicyano-2-(perfluoroheptyl)ethylene, a precursor for synthesizing perfluorocarbon-soluble dyes, which have applications in various nanotechnological processes.
5. Used in Lithography:
METHYL PERFLUOROOCTANOATE is used as a component in investigating the vinyl ether formulations for use in step and flash imprint lithography, a technique employed in the manufacturing of semiconductor devices and other microelectronic components.
6. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, METHYL PERFLUOROOCTANOATE could potentially be used in the pharmaceutical industry for the development of drug delivery systems or as an intermediate in the synthesis of various pharmaceutical compounds due to its unique chemical properties.

InChI:InChI=1/C9H3F15O2/c1-26-2(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 
• 67-56-1 methanol 
• 507-63-1 1-iodoheptadecafluorooctane 
• 307-35-7 perfluorooctyl sulfofluorure 
• 149-73-5 trimethyl orthoformate 
• 3825-26-1 ammonium salt of perfluorooctanoic acid 
• 335-64-8 pentadecafluorooctanoyl chloride 
• 111-11-5 methyl octanate 
• 68555-67-9 Sodium n-perfluorooctanesulfinate 
• 124-07-2 Octanoic acid 

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 
• 335-64-8 pentadecafluorooctanoyl chloride 
• 53511-33-4 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-1-phenylpentane-1,3-dione 
• 335-67-1 Perfluorooctanoic acid 
• 141478-90-2 2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-octanoyl)-cyclohexanone 
• 42268-97-3 N,N-bis-(2-hydroxyethyl)perfluorooctanamide 
• 307-30-2 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol 
• 179116-78-0 1,1-Dichloro-3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoro-1-phenyl-nonan-2-one 
• 128451-14-9 2-chloro-1,1-dicyano-2-(perfluoroheptyl)ethylene 
• 128451-01-4 4-(N,N-dimethylamino)-α-(perfluoroheptyl)-β,β-dicyanostyrene 
• 128451-06-9 4-(N,N-dimethylamino)-2-methyl-α-(perfluoroheptyl)-β,β-dicyanostyrene 
• 128451-02-5 4-(N,N-diethylamino)-α-(perfluoroheptyl)-β,β-dicyanostyrene 
• 128451-05-8 1-pyrrolidino-α-(perfluoroheptyl)-β,β-dicyanostyrene 
• 128451-04-7 4-(4-morpholino)-α-(perfluoroheptyl)-β,β-dicyanostyrene 

Relevant articles and documents

Reaction of Perhalofluoroalkyl Sulfinates With One-Electron Transfer Oxidants. A Facile Method For the Synthesis of Perhalofluorocarboxylic Acids

Reaction of perhalofluoroalkyl sulfinates with one-electron transfer oxidants, such as (NH4)2S2O8, Ce(SO4)2 or H2O2/Fe2+ afforded perhalofluorocarboxylic acids RfCO2H in good yield.

5-PERFLUOROALKYL BIBYCLIC AMIDE ACETALS

A new route to a novel class of bicyclic amide acetals, 5-perfluoroalkyl-4,6-dioxa-1-azabicyclooctanes, is descibed.These compounds are prepared by the acid catalyzed dehydration of N,N-bis(2-hydroxyethyl)-perfluoroalkylamides and are characterized by their lack of reactivity with a variety of electrophiles and nucleophiles relative to the very reactive 5-alkyl bicyclic amide acetals.

Fluoridation process of 1,3- full-fluorine compound 1,3- containing Edipivalic acid ester or dioxane ester

The invention provides a fluorination process of 1,3-dioxolame ester or 1,3-dioxane ester containing perfluorinated compounds. The process comprises the following steps of putting a first fluorinationsolvent and a catalyst into a reaction kettle, wherein the catalyst is selected from one or several of boron trifluoride, cobalt trifluoride, bismuth trifluoride and arsenic trifluoride; dissolving ahydrocarbon substrate and a surfactant in a second fluorination solvent to obtain a raw material solution, wherein the surfactant is selected from one or several of perfluorononanoic acid, perfluorooctane sulfonate and tetrabutylammonium fluoride, and the hydrocarbon substrate is of a structure of a formula (I) or a formula (II); performing fluorination reaction on the raw material liquid and fluorine gas in the reaction kettle to obtain the perfluorinated compounds. In the specific fluorine-containing solvent, the low-cost hydrocarbon compounds are used as starting raw materials; the specialfluorine-containing surfactants and catalysts are used as the assistance so that the fluorine gas and the raw materials are in direct contact to be converted into the perfluorinated compounds. The method is simple; the cost is low; meanwhile, the yield is high.

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.

FLUORINATED IMIDOYLAMIDINES VULCANIZING AGENTS

The invention provides a compound and, tautomeric forms thereof having the formula (I): wherein Rf1 is selected from the group consisting of hydrogen, a straight chain, branched secondary or branched tertiary C1-C20 perfluoroalkyl group optionally containing ether or thioether linkages and C1-C10 perfluoroalicyclic group optionally containing ether or thioether groups; Rf2 is a straight or branched C1-C20 perfluoroalkylene group optionally substituted with ether and thiother linkages; and X is selected from the group consisting of fluorine and formula (II). . The invention also provides perfluoroelastomeric compositions cured with the perfluoroimidoylamidines of the invention as well as combinations of perfluoroimidoylamidines and other curing agents.

Method of recovering fluorinated acid surfactants from adsorbent particles loaded therewith

The present invention provides a method of recovering a fluorinated acid surfactant or salt thereof from adsorbent particles to which said fluorinated acid surfactant has been adsorbed. The method comprises mixing adsorbent particles having adsorbed fluorinated acid surfactant or salt thereof with an alcohol and optionally an acid. The mixture is generally heated to cause esterification of the fluorinated acid surfactant or salt thereof with the alcohol so as to form an ester derivative of the fluorinated acid surfactant, distilling the mixture to form a distillate comprising the ester derivative, separating the ester derivative from the distillate and optionally feeding the remainder of the distillate back into the mixture.

Aggregation Behavior of Mixed Fluorocarbon and Hydrocarbon Molecules in Aqueous Organic Solvents. Nonideality and Ideality of Mixing

The emission spectra of naphthalene labeled hydrocarbons (NpHCn) and fluorocarbons (NpFCn) and anthracene labeled hydrocarbons (AnHCn) and fluorocarbons (AnFCn) in aqueous organic mixed solvents were investigated.The fluorescence spectrum of NpHC16 in dimethyl sulfoxide-water (DMSO-H2O) is dominated by excimer emission due to formation of aggregates.Addition of a fluorocarbon compound with chain length of seven perfluoromethylenes results in a reduction in the excimer emission and an enhancement of monomer emission, suggesting formation of coaggregates.In contrast, addition of a perfluorocarbon compound with chain length of 12 perfluoromethylenes results in no change in the fluorescence spectrum of NpHC16.Similarly, NpFC7 and NpFC12 in DMSO-H2) also exhibit excimer emission exclusively.Fluorescence studies show that hydrocarbon compounds coaggregate with NpFC7 but do not coaggregate with NpFC12.Selective excitation of the naphthalene moiety in the mixture solution of NpHC16 with AnFC7 or in the mixture solution of NpFC7 with AnHC12 exclusively leads to the emission of the anthracene moiety, suggesting that efficient energy transfer between the naphthalene and the anthracene chromophores occurs.On the other hand, for the mixture of NpHC16 with AnFC12 or NpFC12 with AnHC12, no energy tranfer was detected.All these observations indicate that fluorcarbon compounds with short chains can mix with hydrocarbon compounds ideally, while those with long chains behave nonideally.The mixed critical aggregation concentrations of NpHC16 with NpFC7 and with NpFC12 are measured as a function of overall composition of the mixtures, which give insight into yje magnitude of the nonideality of the mixings.

Chlorotrifluoroethylene-derived fluids. I. Model compound synthesis

A series of chlorofluoroalkanes having chlorines on adjacent carbon atoms has been prepared, i.e. n-C5F11CFClCCl3, n-C6F13CFClCCl3, n-C5F11CFClCFCl2, n-C6F13CFClCFCl2, n-C5F11CFClCF2Cl, n-C2F5CFClCFClC3F7 and n-CF3CFClCFClC4F9, by a combination of halogen exchange, dehalogenation and chlorine addition reactions.An attempt to synthesize n-C6F13CFClCF2CFCl2 by the coupling of n-C6F13CFClI with an excess of ICF2CFCl2 under UV radiation in the presence of Hg gave only n-C6F13CFClCFClC6F13 together with CFCl2CF2CF2CFCl2.Under parallel conditions from n-C6F13CFClI and CF2ClCFClI, n-C6F13CFClCFClCF2Cl was obtained in 48percent yield.

Photooxidation of Perhalofluorosulfinates. A Simple and Effective Method for the Synthesis of Perhalofluorocarboxylic Acids and Their Esters from the Corresponding Sulfonyl Fluorides

Photooxidation promoted by ultraviolet irradiation of perhalofluorosulfinates afforded a simple and effective method for the synthesis of perhalofluorocarboxylic acids and their esters from the corresponding sulfonyl fluorides.

Halogenated 1,3-dioxolanes and derivatives

There are disclosed halogenated dioxolanes of a specified formula, dioxoles made therefrom, polymers of the dioxoles, and processes for making the dioxolanes.