21652-58-4

Basic information

• Product Name: 1H,1H,2H-Perfluoro-1-decene
• Synonyms: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-1-decene,99%;1,1,2-Trihydroperfluoro-1-decene;(Perfluoroct-1-yl)ethylene, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodec-1-ene;1H,1H,2H-Heptadecafluorodec-1-ene 97%;1H,1H,2H-Perfluoro-1-decene 99%;(PERFLUOROOCTYL)ETHYLENE;(PERFLUORO-N-OCTYL)ETHYLENE;1-Decene, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-
• CAS NO: 21652-58-4
• Molecular Formula: C₁₀H₃F₁₇
• Molecular Weight: 446.1
• EINECS: 244-503-5
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 21652-58-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 146-147 °C
• Flash Point: >230 °F
• Appearance: clear colorless liquid
• Density: 1.677 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.36mmHg at 25°C
• Refractive Index: n20/D 1.301(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• BRN: 2066558
• CAS DataBase Reference: 1H,1H,2H-Perfluoro-1-decene(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H,2H-Perfluoro-1-decene(21652-58-4)
• EPA Substance Registry System: 1H,1H,2H-Perfluoro-1-decene(21652-58-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1993
• WGK Germany: 3
• TSCA: T
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 21652-58-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

1H,1H,2H-Perfluoro-1-decene is useful in the chemical process of making an electrolyte-phobic surface for next generation nanostructured battery electrodes.

InChI:InChI=1/C10H3F17/c1-2-3(11,12)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)9(23,24)10(25,26)27/h2H,1H2

Upstream product

• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 108-59-8 malonic acid dimethyl ester 
• 105-53-3 diethyl malonate 
• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 2043-54-1 1-iodo-1H,1H,2H,2H-perfluorododecane 
• 30046-31-2 1-iodo-1H,1H,2H,2H-perfluorotetradecane 
• 10192-85-5 potassium acrylate 
• 116-14-3 polytetrafluoroethylene 
• 74-85-1 ethene 
• 354-64-3 Pentafluoroethyl iodide 
• 89807-86-3 2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decan-1-ol 
• 1277151-43-5 dibenzyl 2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl phosphate 
• 64-19-7 acetic acid 
• 79-41-4 poly(methacrylic acid) 

Downstream Products

• 77117-48-7 perfluorooctyl-ethane 
• 74612-30-9 chloro(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)dimethylsilane 
• 106873-72-7 (Z)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-en-1-yl)benzene 
• 82497-73-2 (E)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decen-1-yl)benzene 
• 1423439-31-9 (E)-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decen-1-yl)-4-methoxybenzene 
• 1423439-60-4 C₁₇H₉F₁₇O 
• 77893-59-5 pentafluoroethyl-acetone 
• 495388-46-0 4-((E)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-dec-1-enyl)-2-methyl-benzoic acid methyl ester 

Relevant articles and documents

Siloxane based syntheses of fluorous ethenes and their tandem Heck reactions with aryl iodides

Perfluoroalkyl-ethenes (RfnCHCH2, 6a-c; a, n = 4; b, n = 6; c, n = 8) were prepared in good isolated yields (67-89%) and high purity (GC assay > 98%) from various fluorinated organosilanes in fluoride-anion assisted protodesilylation reactions. The environmentally more benign 'KF/NEt3/H2O' reagent combination introduced here was found as an effective substitute for the commonly used tetrabutylammonium- fluoride trihydrate (TBAF·3H2O) as a fluoride source. Fluorous styrenes ((E)-RfnCHCHAr, 8) were then prepared in good isolated yields (58-93%/iodoarene) and purities (GC assay > 95%) with the Pd(0) catalyzed Heck coupling of iodoarenes (Ar-I, 7) and perfluoroalkyl-ethenes generated in situ by the fluoride assisted cleavage of (β-perfluoroalkyl- α-iodo-ethyl)-siloxane ([RfnCH2CH(I)SiMe 2]2O, 3) precursors in DMF solution at elevated temperatures. They are accessible by the one-pot reaction of dimethylvinylchlorosilane (CH2CHSiMe2Cl, 2) and perfluoroalkyl iodides (Rfn-I, 1) as we reported earlier. Similarly, the radical chain addition of C8F17I to CH 2CHSi(OMe)3 (9) gave (β-perfluorooctyl-α-iodo- ethyl)-trimethoxysilane ([C8F17CH2CH(I)]Si(OMe) 3, 10) in good yield, which then was reacted with silica gel in dry toluene to obtain an SiO2-bonded (perfluorooctyl)ethene surrogate [silica(O)3SiCH(I)CH2C8F17, 11]. The fluoride assisted cleavage of 11 and tandem Heck reaction with iodobenzene afforded the appropriate cross-coupled product (E)-C8F 17CHCHPh.

PROCESS FOR PRODUCING FLUORINATED (METH)ACRYLIC ESTER

A mixture of fluoroalkyl iodides of the formula C2F5(CF2CF2)nI ( n is an integer of ≥0) wherein the sum of such fluoroalkyl iodides of n=3 and n=4 contained is ≥85 mol% is provided. This mixture is subjected to an ethylene addition step and an esterification step, and C2F5(CF2CF2)nCH=CH2 and C2F5(CF2CF2)nCH2CH2OH are removed. Thus, there can be obtained a mixture of fluorine-containing (meth)acrylic esters of the formula C2F5(CF2CF2)nCH2CH2OCOCR1=CH2 (wherein R1 represents a hydrogen atom or a methyl group, and n is an integer of ≥0) wherein the content of impurities (namely, olefins of the formula C2F5(CF2CF2)nCH=CH2 and alcohols of the formula C2F5(CF2CF2)nCH2CH2OH) is low.

PROCESS FOR PRODUCING FLUORINATED ACRYLIC ESTER

A mixture of fluorine-containing acrylic esters represented by CF3(CF2)nCH2CH2OCOCR1=CH2 wherein R1 is a hydrogen atom, a methyl group or a halogen atom and "n" is an integer of at least zero is subjected to distillation under such conditions that the esters are not polymerized, so as to give a mixture of the esters with a less content of impurities (that is, olefins represented by CF3(CF2)nCH=CH2 and alcohols represented by CF3(CF2)nCH2CH2OH) at a high yield.