42977-21-9

Basic information

• Product Name: BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE
• Synonyms: BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE;BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULPHIDE;bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl) disulphide;Bis(1H,1H,2H,2H-perfluorodecyl)disulphide 97%;Bis(1H,1H,2H,2H-perfluorodecyl)disulphide97%
• CAS NO: 42977-21-9
• Molecular Formula: C₂₀H₈F₃₄S₂
• Molecular Weight: 958.35
• EINECS: 256-031-7
• Mol File: 42977-21-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 75
• Boiling Point: 376.8°Cat760mmHg
• Flash Point: 181.7°C
• Appearance: /
• Density: 1.673g/cm³
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.326
• CAS DataBase Reference: BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE(42977-21-9)
• EPA Substance Registry System: BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE(42977-21-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 42977-21-9(Hazardous Substances Data)

Usage

Uses

Bis(1H,1H,2H,2H-perfluorodecyl)disulfide (CAS# 42977-21-9) is a dropwise condensation promoter, and a surface modifier used in triple quadrupole mass spectrometers.

InChI:InChI=1/C20H8F34S2/c21-5(22,7(25,26)9(29,30)11(33,34)13(37,38)15(41,42)17(45,46)19(49,50)51)1-3-55-56-4-2-6(23,24)8(27,28)10(31,32)12(35,36)14(39,40)16(43,44)18(47,48)20(52,53)54/h1-4H2

Upstream product

• 34143-74-3 1H,1H,2H,2H-Perfluorodecanethiol 
• 1318074-51-9 6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(2,4-dimethoxybenzyl)-1,3-dihydroindol-2-one 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 1318074-65-5 6-methoxy-3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-benzyl-1,3-dihydroindol-2-one 
• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 534-18-9 sodium trithiocarbonate 
• 125640-21-3 S-[2-(perfluorooctyl)ethyl]thioacetate 
• 76598-00-0 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octanethiosulfonic acid S-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl) ester 
• 4393-11-7 N-benzyl-1-(furan-2-yl)methanimine 
• 1318074-61-1 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one 
• 22483-21-2 isobutylidenebenzylamine 
• 1318074-60-0 5-bromo-3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-6-methoxy-1,3-dihydroindol-2-one 
• 141120-47-0 benzyl-pyridin-3-ylmethylene-amine 
• 1318074-59-7 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-6-methoxy-1,3-dihydroindol-2-one 

Downstream Products

• 34143-74-3 1H,1H,2H,2H-Perfluorodecanethiol 
• 1318074-65-5 6-methoxy-3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-benzyl-1,3-dihydroindol-2-one 
• 1318074-64-4 6-methoxy-3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-p-methoxybenzyl-1,3-dihydroindol-2-one 
• 1318074-61-1 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one 
• 1318074-56-4 6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-benzyl-1,3-dihydroindol-2-one 
• 1318074-57-5 C₂₆H₁₈F₁₇NO₂S 
• 1318074-54-2 6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-p-methoxybenzyl-1,3-dihydroindol-2-one 
• 1318074-55-3 C₂₇H₂₀F₁₇NO₃S 
• 1318074-52-0 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one 
• 1318074-51-9 6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(2,4-dimethoxybenzyl)-1,3-dihydroindol-2-one 

Relevant articles and documents

Oxidation chemistry of perfluoroalkyl-segmented thiols, disulfides, thiosulfinates and thiosulfonates: The role of the perfluoroalkyl group in searching out new chemistry

The oxidation chemistry of perfluoroalkyl-segmented thiols, RF-R-SH (1), thiosulfinates, RF-R-S(O)S-R-RF (3), thiosulfonates, RF-R-S(O2)S-R-RF (4) and disulfides, RF-R-SS-R-RF (5) (in which RF=n-C6F13 or n-C8F17 and R=CH2CH2) is studied herein. Base catalyzed reaction of C6 thiol 1 with hydrogen peroxide gives pure disulfide 5, quantitatively. Other, less suitable methods for the oxidation of thiol 1 are also examined and compared. Selective oxidation of disulfide 5 by peroxy acids in chlorinated solvents gives excellent yields of thiosulfinate 3. Unlike their hydrocarbon analogues, which are unstable to heating or storage, the RF-segmented thiosulfinates 3 are relatively stable, crystalline compounds. Selective oxidation of 3 by sodium metaperiodate gives thiosulfonate 4 in high yield. Side reactions intervene with unfavorable conditions, or when peroxy acetic acid in acetic acid is used as oxidant,. Oxidation of 5 by hydrogen peroxide in low conversion gives 4 and two new compounds, 8 and 9. Compound 8 is n-C6F13S(O)2CH2CH2C 6F13 (probably the sulfinate ester and not the sulfone), and 9 is most likely the O,S-sulfenyl sulfinate or, possibly an isomer, the vic-disulfoxide. A free radical chain mechanism is proposed for conversion of 4 (or 9) to 8. Compounds 8 and 9 are stable in solution and are identified by MS/GC. In 3, 4 and 5, the ν CH bands correlate with NMR of CH2 at C(1) and C(2) positions, both 1H and 13C NMR. The RF-segment in these unique sulfur compounds enhances their utility and modifies their chemical and physical properties in important and interesting ways.

Exploiting Sm(ii) and Sm(iii) in SmI2-initiated reaction cascades: Application in a tag removal-cyclisation approach to spirooxindole scaffolds

A tag removal-cyclisation sequence is described that is initiated by reduction using a Sm(ii) species and completed by a Sm(iii) Lewis acid that is formed in an earlier stage. Therefore, the reaction cascade utilises both oxidation states of a samarium reagent in discrete steps and allows access to privileged, pyrrolidinyl-spirooxindole scaffolds and analogues inspired by the anti-cancer natural product spirotryprostatin A. The Royal Society of Chemistry 2011.

Phase transfer synthesis of symmetrical di-terminally perfluorinated alkyl trithiocarbonates

Symmetrical di-terminally perfluorinated alkyl trithiocarbonates having the formula [F(CF2)n(CH2)mS]2CS (n = 4,6,8 m = 2 and n = 6,8 m = 11) were prepared in good yield under phase-transfer catalytic conditions starting from perfluoroalkyl alkyl iodides F(CF2)n(CH2)mI.