89889-20-3

Basic information

• Product Name: 3-(PERFLUOROHEXYL)PROPYL IODIDE
• Synonyms: 3-(PERFLUOROHEXYL)PROPYL IODIDE;4,4,5,5,6,6,7,7,8,8,9,9,9-TRIDECAFLUORONONYL IODIDE;1H,1H,2H,2H,3H,3H-PERFLUORONONYL IODIDE;1,1,1,2,2,3,3,4,4,5,5,6,6-TRIDECAFLUORO-9-IODONONANE;1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-9-iodononane, 3-(Perfluorohexyl)propyl iodide, 1H,1H,2H,2H,3H,3H-Perfluorononyl iodide
• CAS NO: 89889-20-3
• Molecular Formula: C₉H₆F₁₃I
• Molecular Weight: 488.03
• Mol File: 89889-20-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 214.9°C at 760 mmHg
• Flash Point: 93.1°C
• Appearance: /
• Density: 1.827g/cm³
• Vapor Pressure: 0.223mmHg at 25°C
• Refractive Index: n20/D 1.369
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 3-(PERFLUOROHEXYL)PROPYL IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(PERFLUOROHEXYL)PROPYL IODIDE(89889-20-3)
• EPA Substance Registry System: 3-(PERFLUOROHEXYL)PROPYL IODIDE(89889-20-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 89889-20-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6F13I/c10-4(11,2-1-3-23)5(12,13)6(14,15)7(16,17)8(18,19)9(20,21)22/h1-3H2

Upstream product

• 80806-68-4 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol 
• 355-43-1 n-perfluorohexyl iodide 
• 83311-03-9 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate 
• 38550-44-6 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-iodononan-1-ol 

Downstream Products

• 80793-18-6 3-(perfluorohexyl)prop-1-ene 
• 89889-21-4 3-(F-Hexyl)-1-methoxypropane 
• 80793-20-0 (E)-4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluoro-non-2-ene 
• 80806-68-4 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol 
• 910660-79-6 benzyl-bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-amine 
• 910660-90-1 bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-(1-methyl-2-phenyl-ethyl) ester 
• 910660-96-7 Bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-((2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester 
• 942056-53-3 C₁₉H₁₉F₁₃O₂ 
• 852527-60-7 9-azido-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorononane 
• 34451-26-8 2-perfluorohexylethanethiol 
• 917379-65-8 trifluoro-methanesulfonic acid 6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-2-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-undecyl ester 

Relevant articles and documents

Preparation of (perfluoroalkyl)alkane thiols via Zemplén deacylation of fluorous (perfluoroalkyl)alkyl thioacetates

Convenient and robust synthesis of (perfluoroalkyl)alkane thiols [(CnF2n+1(CH2)mSH); m/n = 3/4,6,8,10, 4a-d; m/n = 2/6, 8; m/n = 1/1,2,3,7,8H, 12a-e] was developed starting from commercially available fluorous alcohols (1a-d, 5, 9a-e). The intermediate (perfluoroalkyl)alkyl iodides and/or sulfonates were reacted with potassium thioacetate in DMF, and the resulting thioacetates were deacetylated by a Zemplén analogue reaction. The (perfluoroalkyl)alkane thiols were obtained in good overall yields and high purity.

Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols

N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase silica gel column (Fluorous Solid Phase Extraction; FSPE). The FDMTC groups were readily removed by oxidation with m-chloroperbenzoic acid (m-CPBA) and subsequent hydrolysis with KHCO3.