55716-11-5

Basic information

• Product Name: 2,2,3,3,5,5,6,6-octafluoro-4-(pentafluoroethyl)morpholine
• Synonyms: 2,2,3,3,5,5,6,6-Octafluoro-4-(pentafluoroethyl)morpholine; morpholine, 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,2,2,2-pentafluoroethyl)-
• CAS NO: 55716-11-5
• Molecular Formula: C₆F₁₃NO
• Molecular Weight: 349.0495
• Mol File: 55716-11-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 41.1°C at 760 mmHg
• Density: 1.82g/cm³
• Vapor Pressure: 412mmHg at 25°C
• Refractive Index: 1.292
• CAS DataBase Reference: 2,2,3,3,5,5,6,6-octafluoro-4-(pentafluoroethyl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,3,3,5,5,6,6-octafluoro-4-(pentafluoroethyl)morpholine(55716-11-5)
• EPA Substance Registry System: 2,2,3,3,5,5,6,6-octafluoro-4-(pentafluoroethyl)morpholine(55716-11-5)

Safety Data

• Hazardous Substances Data: 55716-11-5(Hazardous Substances Data)

Upstream product

• 33611-43-7 methyl 3-morpholinopropionate 
• 89841-36-1 4-<2-(Trimethylsiloxy)ethyl>morpholine 
• 20120-24-5 ethyl 3-morpholinopropionate 
• 5471-53-4 methyl 4-morpholinobutanoate 
• 100-37-8 2-(Diethylamino)ethanol 
• 139-87-7 ethyldiethanolamine 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 33611-45-9 methyl 3-methyl-3-morpholinylpropionate 
• 20120-26-7 (2-methyl-3-morpholin-4-yl)propionic acid methyl ester 
• 110073-17-1 2-morpholinopropionic acid methyl ester 
• 30280-35-4 N,N-diethylglycine methyl ester 

Relevant articles and documents

Electrochemical fluorination of several methyl and/or ethyl esters of morpholino-substituted carboxylic acids

Seven methyl and/or ethyl esters of carboxylic acids (-CH2CH2C(O)OEt, -CH2CH2CH2C(O)OMe, -CH2CH2CH2C(O)OEt, -CH(C2H5)C(O)OMe, -CH(n-C3H7)C(O)OMe, -CH2CH2CH2CH2C(O)OEt and -CH2CH2CH2CH2CH2C(O) OEt) having a morpholino group were subjected to electrochemical fluorination (ECF). On ECF, the corresponding perfluoroacid fluorides bearing a perfluoromorpholino group were obtained in fair to good yields. Yields of the targeted perfluoromorpholino-containing perfluoroacid fluorides were influenced by the α-bond cleavage of the carboxylic acid and also by the kind of alkyl group of the carboxylic acid (the latter offering the possibility of cyclization side reactions). Perfluorooxolanes were formed as a major cyclization by-product from the ECF of morpholino-substituted carboxylic acids when the chain length of the alkyl group of the carboxylic acids had a carbon number of three or more and the structure of the alkyl group was branched in such a way as to allow cyclization. Perfluorodioxolanes were obtained in only small yields as the specific cyclization products when the ethyl esters of carboxylic acids were subjected to ECF. Spectroscopic data, as well as physicochemical properties, are described for the new perfluoroheterocyclic compounds with a perfluoromorpholino group that were produced.

Electrochemical fluorination of di- and tri-(2-hydroxyethyl)-substituted alkylamines

Several 2-(hydroxyethyl)-substituted alkylamines like 1,4-bis(2-hydroxyethyl)piperazine, N,N-bis(2-hydroxyethyl)methylamine, N,N-bis(2-hydroxyethyl)ethylamine, and N,N,N-tris(2-hydroxyethyl)amine as well as their derivatives (HCl salts, a borate and trimethylsilylethers) were subjected to electrochemical fluorination. From 1,4-bis(2-hydroxyethyl)piperazine, F-[1,4-bis(fluorocarbonylmethyl)piperazine] was obtained in low yield. In the fluorination of N,N-bis(2-hydroxyethyl)alkylamines and N,N,N-tris(2-hydroxyethyl)amine, cyclization occurred extensively, affording large quantities of F-morpholine derivatives. However, F-N,N-bis(fluorocarbonylmethyl)methylamine was obtained from the former in low, isolated yield.

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).