cas 1691-99-2, N-Ethyl-N-(2-hydroxyethyl)perfluorooctylsulphonamide

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Synthesis and structure of environmentally relevant perfluorinated sulfonamides
Alkylated perfluorooctanesulfonamides are compounds of environmental concern. To make these compounds available for environmental and toxicological studies, a series of N-alkylated perfluorooctanesulfonamides and structurally related compounds were synthesized by reaction of the corresponding perfluoroalkanesulfonyl fluoride with a suitable primary or secondary amine. Perfluoroalkanesulfonamidoethanols were obtained from the N-alkyl perfluoroalkanesulfonamides either by direct alkylation with bromoethanol or alkylation with acetic acid 2-bromo-ethyl ester followed by hydrolysis of the acetate. N-Alkyl perfluorooctanesulfonamidoacetates were synthesized in an analogous way by alkylation of N-alkyl perfluoroalkanesulfonamides with a bromo acetic acid ester, followed by basic ester hydrolysis. Alternatively, N-alkyl perfluoroalkanesulfonamides can be alkylated with an appropriate alcohol using the Mitsunobu reaction. Perfluorooctanesulfonamide was synthesized from the perfluorooctanesulfonyl fluoride via the azide by reduction with Zn/HCl. All perfluorooctanesulfonamides contained linear as well as branched C8F17 isomers, typically in a 10:1 to 30:1 ratio. The crystal structures of N-ethyl and N,N-diethyl perfluorooctanesulfonamide show that the S-N bond has considerable double bond character. This double bond character results in a significant rotational barrier around the S-N bond (ΔG≠ = 62-71 kJ mol-1) and a preferred solid state and solution conformation in which the N-alkyl groups are oriented opposite to the perfluorooctyl group to minimize steric crowding around the S-N bond.
Lehmler, Hans-Joachim,Rama Rao,Nauduri, Dhananjaya,Vargo, John D.,Parkin, Sean
p. 595 - 607
(2007)
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Chemical Properties

Appearance/Colour :Under room temperature , it is white or yellowish waxy solid and turned into amber liquid after being melted.
Melting Point: 55-65°C
Boiling Point: 316.7 °C at 760 mmHg
Flash Point:145.4 °C
Density: 1.653 g/cm³
Solubility:Chloroform (Slightly), DMSO, Ethyl Acetate (Slightly), Methanol (Slightly)
Storage Temp.:Refrigerator, under inert atmosphere
Vapor Pressure: 3.39E-05mmHg at 25°C
Refractive Index: 1.347
PKA: 14.10±0.10(Predicted)
PSA: 65.99000
LogP: 5.67810

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1691-99-2

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Chemical Properties

Appearance/Colour :Under room temperature , it is white or yellowish waxy solid and turned into amber liquid after being melted.

Melting Point: 55-65°C

Boiling Point: 316.7 °C at 760 mmHg

Flash Point:145.4 °C

Density: 1.653 g/cm³

Solubility:Chloroform (Slightly), DMSO, Ethyl Acetate (Slightly), Methanol (Slightly)

Storage Temp.:Refrigerator, under inert atmosphere

Vapor Pressure: 3.39E-05mmHg at 25°C

Refractive Index: 1.347

PKA: 14.10±0.10(Predicted)

PSA: 65.99000

LogP: 5.67810

Global suppliers and manufacturers of 1691-99-2total 43 suppliers on LookChem

Article Database

1691-99-2

Articles about 1691-99-2Total 1 be found

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Chemical Properties

Appearance/Colour :Under room temperature , it is white or yellowish waxy solid and turned into amber liquid after being melted.

Melting Point: 55-65°C

Boiling Point: 316.7 °C at 760 mmHg

Flash Point:145.4 °C

Density: 1.653 g/cm3

Solubility:Chloroform (Slightly), DMSO, Ethyl Acetate (Slightly), Methanol (Slightly)

Storage Temp.:Refrigerator, under inert atmosphere

Vapor Pressure: 3.39E-05mmHg at 25°C

Refractive Index: 1.347

PKA: 14.10±0.10(Predicted)

PSA: 65.99000

LogP: 5.67810

Global suppliers and manufacturers of 1691-99-2total 43 suppliers on LookChem

Density: 1.653 g/cm³