359-70-6

Basic information

• Product Name: Perfluorotriethylamine
• Synonyms: PERFLUOROTRIETHYLAMINE;PENTADECAFLUOROTRIETHYLAMINE;TRIS(PENTAFLUOROETHYL)AMINE;1,1,2,2,2-Pentafluoro-N,N-bis(1,1,2,2,2-pentafluoroethyl)ethanamine;1,1,2,2,2-pentafluoro-n,n-bis(pentafluoroethyl)-ethanamin;Ethanamine, 1,1,2,2,2-pentafluoro-N,N-bis(pentafluoroethyl)-;n,n-bis(pentafluoroethyl)-1,1,2,2,2-pentafluoroethanamine;n,n-bis(pentafluoroethyl)-1,1,2,2,2-pentalfluoro-ethanamin
• CAS NO: 359-70-6
• Molecular Formula: C₆F₁₅N
• Molecular Weight: 371.05
• EINECS: 206-632-5
• Mol File: 359-70-6.mol

Chemical Properties

• Melting Point: -116.95°C
• Boiling Point: 68-69 °C743 mm Hg(lit.)
• Appearance: /
• Density: 1.736 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.15 psi ( 20 °C)
• Refractive Index: n20/D 1.262(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -27.46±0.50(Predicted)
• CAS DataBase Reference: Perfluorotriethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Perfluorotriethylamine(359-70-6)
• EPA Substance Registry System: Perfluorotriethylamine(359-70-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3267 8/PG III
• WGK Germany: 3
• RTECS: KH2155170
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 359-70-6(Hazardous Substances Data)

Usage

Uses

Used in Toxicity Testing:
Perfluorotriethylamine is used as a testing agent for toxicity experiments, helping to determine the potential harmful effects of substances on living organisms. Its chemical properties make it suitable for use in various toxicity assays, including those that assess the impact on aquatic life, terrestrial organisms, and human health.
Used in Cytotoxicity Assessments:
In the field of cell biology and pharmaceutical research, Perfluorotriethylamine is utilized as a tool in cytotoxicity tests. These tests are essential for evaluating the potential harmful effects of drugs, chemicals, or other substances on cells. Perfluorotriethylamine aids in understanding the mechanisms of cell damage and death, which is crucial for developing safe and effective treatments.
Used in Genotoxicity Studies:
Perfluorotriethylamine is also employed in genotoxicity experiments, which focus on the assessment of DNA damage caused by various agents. Genotoxicity is a critical aspect of safety evaluation, as DNA damage can lead to mutations, which may result in cancer or other genetic disorders. The use of Perfluorotriethylamine in these studies helps researchers identify potential genotoxic agents and understand their mechanisms of action.
Used in Pyrolysis Experiments:
In the field of materials science and chemical engineering, Perfluorotriethylamine is used in pyrolysis experiments. Pyrolysis is a thermochemical decomposition process that occurs in the absence of oxygen, and it is widely used for the conversion of organic materials into simpler compounds. Perfluorotriethylamine's thermal stability and chemical inertness make it an ideal candidate for studying the pyrolysis of various substances, providing valuable insights into the underlying chemical reactions and potential applications of the resulting products.

InChI:InChI=1/C6F15N/c7-1(8,9)4(16,17)22(5(18,19)2(10,11)12)6(20,21)3(13,14)15

Upstream product

• 121-44-8 triethylamine 
• 106815-18-3 methyl 2-diethylamino-propionate 
• 5351-01-9 methyl 3-(N,N-diethylamino)propionate 
• 68-05-3 tetraethylammonium iodide 
• 132917-41-0 Methyl 2-(N'-methyl-N-piperazinyl)propionate 
• 31084-16-9 methyl 2-methyl-3-(N,N-diethylamino)propionate 
• 357-83-5 N-(2-chloro-1,1,2-trifluoroethyl)diethylamine 
• 309-88-6 hexafluoropropene-diethylamine adduct 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 100-37-8 2-(Diethylamino)ethanol 
• 7664-39-3 hydrogen fluoride 
• 10026-18-3 cobalt(III) fluoride 
• 530098-58-9 methyl 4-ethylpiperazin-1-ylacetate 
• 5308-25-8 4-ethylpiperazine 

Relevant articles and documents

On the formation of surface active by-products during the electrochemical fluorination of tertiary amines

The electrochemical fluorination (ECF) of 2-phenyl-3,4-dimethylmorpholine led to the solubilization of the perfluoro products and HF foaming, which may be traced back to the formation of partially fluorinated, HF-soluble compounds which exhibit surface activity in HF.Some of the perfluoro products contain an asymmetric carbon atom attached directly to a cyclohexyl ring.This asymmetric centre leads to the non-equivalence of the fluorines bound to carbon atoms 2 and 6, respectively, of the cyclohexyl ring allowing them to be distinguished in the 19F NMR spectra.

An efficient high-yield synthesis for perfluorinated tertiary alkyl amines

We wish to report a high-yield synthesis of perfluorinated tertiary amines from their hydrocarbon analogues by direct fluorination. Yields up to 70%, with high purities, have been obtained from certain tertiary amines. This technique will likely develop into a new general method for producing perfluorinated amines.

Simons electrochemical fluorination of substituted homopiperazines(hexahydro-1,4-diazepines) and piperazines

Simons electrochemical fluorination (ECF) of 1,4-dimethyl-1,4-homopiperazine, methyl 4-ethylhomopiperazin-1-ylacetate and 1,4-bis(methoxycarbonylmethyl)-1,4-homopiperazine was studied. For comparison, ECF of three piperazines with a N-(methoxycarbonylmethyl) group(s) was also studied. ECF of 1,4-dimethyl-1,4-homopiperazine gave a low yield of corresponding perfluoro(1,4-dimethyl-1,4-homopiperazine) together with perfluoro(2,6-diaza-2,6-dimethylheptane) as the major product. Corresponding perfluoro(homopiperazines) with mono- and/or di-(fluorocarbonyldifluoromethyl) groups [-CF2C(O)F] at the 1- and/or 4-position were formed in low yields from methyl 4-ethylhomopiperazin-1-ylacetate and 1,4-bis(methoxycarbonylmethyl)-1,4-homopiperazine, respectively. These new seven-membered perfluoro(1,4-dialkyl-1,4-homopiperazines) were accompanied by the formation of mono- and/or di-basic linear perfluoroacid fluorides resulting from the C-C bond scission at the 2- and 3-positions of the ring. From mono- and/or di-N-(methoxycarbonylmethyl)-substituted piperazines, corresponding perfluoropeperazines having the acid fluoride group(s) were formed in low yields.

Electrochemical fluorination of 1-ethylpiperazine and 4-methyl- and/or 4-ethylpiperazinyl substituted carboxylic acid methyl esters

Electrochemical fluorination (ECF) of 1-ethylpiperazine and eight methyl esters of 4-methyl- and/or 4-ethylpiperazinyl substituted carboxylic acids were studied. Corresponding perfluoro(4-fluoro-1-ethylpiperazine) was obtained from 1-ethylpiperazine in a small yield along with perfluoro(1-methyl-3-ethylimidazolidine), perfluoro[2-(N′,N′-difluoroaminoethyl)-N,N-diethylamine)] and perfluorotriethylamine. The corresponding mono-basic perfluoroacid fluorides with a perfluoro(4-alkylpiperazinyl) group were obtained in fair to good yields from the fluorination of methyl esters of 4-alkylpiperazinyl-substituted carboxylic acids. Yields of the targeted perfluoro(4-alkylpiperazinyl) group containing perfluorocarboxylic acid fluorides varied depending on both the type of N-alkyl (alkyl=CH3- or C2H5-) group at the 4-position and the (ω-methoxycarbonylalkyl) group at the 1-position of the piperazine ring of the substrate. Higher yields of perfluoroacid fluorides were obtained by the ECF of 4-ethyl substituted piperazine derivatives than of the 4-methyl substituted piperazine derivatives when 4-alkylpiperazines with the same carboxylic acid ester group were fluorinated electrochemically. Spectroscopic data as well as physical properties are described for new perfluoro(1,4-dialkylpiperazines) and N-containing perfluorocarboxylic acids with a perfluoropiperazinyl group.

Electrochemical fluorination of (N,N-dialkylamino)alcohols

Series of amino alcohols including 2-(N,N-dialkylamino)ethanols, 3-(N,N-dimethylamino)propanol and 4-(N,N-dimethylamino)butanol were subjected to electrochemical fluorination. In the case of 2-(N,N-dialkylamino)ethanols, the F-(2-N,N-dialkylamino)acetyl fluorides were obtained in fair to good yields. Yields of each target compound were strongly dependent on the kind of the dialkylamino group. Cyclic amines having an N-(2-hydroxylethyl) group afforded the corresponding F-[N-(c-alkylamino)-substituted acetyl fluorides]. Their yields were generally better than those of acyclic analogs. Several 2-(N,N-dialkylamino)ethanols and 3-(N,N-dimethylamino)propanol were converted into the corresponding trimethylsilylethers, aminoalkyl methyl carbonates and bis-aminoalkyl carbonate, respectively, and they were subjected to fluorination for a comparison of the yield with that obtained from that of the parent aminoalcohol.

Technology for the preparation of perfluoro-organic compounds

Fluorination by elemental fluorine of fluorine-containing alkenes, alkanes, ethers and tertiary amines was investigated, aimed at obtaining the perfluorinated analogs. The factors affecting yield of the target compounds were studied. Elements of technology were elucidated.

Mechanistic studies on the electrochemical fluorination of trialkylamines and tetraalkylammonium salts

The comparative electrochemical fluorination (ECF) of selected trialkylamines and tetraalkylammonium salts was studied in order to obtain experimental data allowing a precise valuation of the ECF mechanism. The results of the investigation favour the ECF mechanism already proposed by Simons, via oxidation of F- .(HF)n to F and nHF, as probably the only relevant electrochemical process at the anode. For the first time some experimental proof has been obtained that a direct electrochemical oxidation of the substrate can be ruled out as a decisive step in ECF.

The electrochemical fluorination of N-containing carboxylic acids (Part 4). Fluorination of methyl 3-dialkylamino-isobutyrates and methyl 3-dialkylamino-n-butyrates

Several methyl esters of 3-dialkylamino-substituted n- and isobutyric acids have been subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides.Dimethyl, diethyl, pyrrolidino, morpholino, piperidino and N-methylpiperazino groups were investigated as dialkylamino substituents.The structure/yield relationship was evaluated both in terms of the structure of the acid and the kind of amino group, respectively.Better yields of perfluoroacid fluorides were obtained from methyl esters having isobutyric acid skeletons than those having n-butyric acid groups, and from the acids containing cyclic amino groups than those containing acyclic ones.

On the electrochemical fluorination of quaternary ammonium compounds. Part 1. Tetraalkyl ammonium salts

Tetraalkylated ammonium compounds, which are known to be very stable towards oxidative attack, can be electrofluorinated readily to yield perfluoro tertiary amines.Other than the enhanced formation of gaseous cleavage products, the electrofluorination proceeds similarly to that of other tertiary amines.

The electrochemical fluorination of nitrogen-containing carboxylic acids. Fluorination of methyl esters of 3-dialkylamino propionic acids

Six methyl esters of 3-dialkylamino-substituted propionic acids were subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides.The following dialkylamino substituents were investigated: diethylamino, di-n-propylamino, di-n-butylamino, pyrrolidino, morpholino and piperidino groups.These perfluoroacid fluorides, which were obtained in fair yields, are considered to be prospective key precursors for preparing soft-type (degradable) fluorochemicals.The salts show a considerable lowering of surface tension in aqueous solution.Thephysical properties of all the perfluoroacid fluorides obtained are reported, together with their spectroscopic data (19F NMR, mass and IR spectra).