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

Description

BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE, with the CAS number 42977-21-9, is a chemical compound known for its unique properties as a dropwise condensation promoter and a surface modifier. It plays a significant role in enhancing the efficiency and performance of various applications across different industries.

Uses

Used in Chemical Synthesis:
BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE is used as a dropwise condensation promoter for facilitating the condensation reactions in chemical synthesis processes. Its ability to promote condensation reactions leads to improved reaction rates and increased yield of desired products.
Used in Mass Spectrometry:
In the field of analytical chemistry, BIS(1H,1H,2H,2H-PERFLUORODECYL)DISULFIDE is used as a surface modifier for triple quadrupole mass spectrometers. Its application in this context helps to enhance the performance of the mass spectrometer by improving ion transmission and detection efficiency, leading to more accurate and reliable analytical results.

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

• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 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 
• 34143-74-3 1H,1H,2H,2H-Perfluorodecanethiol 
• 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 
• 1318074-82-6 benzylidene-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)benzyl]amine 
• 1318074-58-6 6-methoxy-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-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 
• 1318074-51-9 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 

Downstream Products

• 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 
• 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 
• 1318074-54-2 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 
• 1318074-56-4 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 
• 1318074-61-1 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 
• 1318074-64-4 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 
• 1318074-65-5 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 
• 34143-74-3 1H,1H,2H,2H-Perfluorodecanethiol 

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.

Preparation, reactions and physical properties of segmented 2-(perfluoroalkyl)ethanesulfinic acids and their derivatives. the role of the perfluoroalkyl group in finding new and useful compounds and in searching out new chemistry

2-(Perfluoroalkyl)ethanesulfinic acids of the formula RFCH2CH2SO2H (2, where RF=n-C6F13, or n-C8F17) are synthesized from the thiol, RFCH2CH2SH (1). These segmented acids 2 have sharp melting point (mp) and can be recrystallized. The C6 or C8 perfluoroalkyl group confers unusual "fluophilic" properties to acids 2 and their derivatives. Water solutions of acids 2 and their Na, K, Cs and Bu4N salts are highly surface active and stable for several days, and are more effective in reducing surface tension at the air/water interface than sodium n-perfluorooctanesulfonate (10). Sodium salts 2 (C6, C8) are converted to K and Cs salts by methathesis in high yield. However, the amphiphilic Bu4N salts of 2 (C6, C8) are best prepared in a biphasic system (C6, 99.6% yield). Acids 2 are synthesized by three methods. (1) Oxidation of the C8 thiol 1 (at -35°C) by m-CPBA gives acid 2 (C8) in 73% yield and unwanted disulfide (3) in 27% yield. The bulky, strongly electronegative RF group of 1 may slow oxidation of the RSOH (intermediate) to allow disproportionation with RSH into disulfide 3 and water. (2) Hydrolysis of RFCH2CH2SO2SCH2CH 2RF (4) with strong base gives salt 2 (C6, or C8; 92% yield). (3) Heating sulfone, RFCH2CH2SO2CH2CH 2Y (8) with a base (M2CO3) eliminates RFCH2CH2SO2M (2, M=Na, K, Cs) in 95-100% yield (C6, C8). Alternatively, 8 with the sodium thiolate of 1 gives RFCnH2nSCH2CH2Y (7, 90%) and sodium salt 2 (C6, 95%). Conjugate addition of the RFCH2CH2SO2- to CH2CHY gives sulfones 8, and RFCH2CH2SO2- adds stereospecifically to cyclohexene oxide, giving the trans-adduct 13. RFCH2CH2SO2H (2), with azo initiator, telomerizes acrylamide to a water-soluble, surface active product.