38565-52-5

Usage

Uses

Used in Chemical Industry:
3-PERFLUOROHEXYL-1,2-EPOXYPROPANE is used as a key component in the production of fluorinated polymers and coatings for its exceptional chemical and thermal stability, which provides these materials with enhanced durability and resistance to harsh conditions.
Used in Specialty Material Synthesis:
In the synthesis of specialty materials, 3-PERFLUOROHEXYL-1,2-EPOXYPROPANE serves as a building block for creating surfactants, lubricants, and pharmaceuticals, leveraging its unique properties to enhance the performance of these products.
Used in Environmental and Health Considerations:
3-PERFLUOROHEXYL-1,2-EPOXYPROPANE is used as a subject of study and regulation due to concerns about its potential environmental and health impacts. As a perfluorinated compound, it has been associated with persistence, bioaccumulation, and toxicity, necessitating careful handling and disposal to mitigate risks to human health and the environment.

InChI:InChI=1/C9H5F13O/c10-4(11,1-3-2-23-3)5(12,13)6(14,15)7(16,17)8(18,19)9(20,21)22/h3H,1-2H2

Upstream product

• 38550-44-6 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-iodononan-1-ol 
• 83310-90-1 2-Iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate 
• 591-87-7 Allyl acetate 
• 355-43-1 n-perfluorohexyl iodide 
• 107-18-6 allyl alcohol 

Downstream Products

• 1262880-14-7 C₂₁H₁₈F₂₆NO₅S^(1-)*Na⁽¹⁺⁾ 
• 1262880-17-0 C₂₀H₁₆F₂₆NO₅S^(1-)*Li⁽¹⁺⁾ 
• 77893-60-8 tridecafluorohexyl-acetone 
• 107650-06-6 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononane-1,2-diol 

Relevant academic research and scientific papers

Highly selective synthesis of [(perfluoroalkyl)methyl]oxiranes (by the addition of iodoperfluoroalkanes to allyl acetate)

Mixtures of regioisomeric adducts of monoiodoperfluoroalkanes RF-I (RF = C4F9, C6F13, C8F17) with allyl acetate, RFCH2CHICH2OAc (1a-1c) and rearranged adducts RFCH2CH(OAc)-CH2I (2a-2c), were converted chemoselectively to the corresponding oxiranes RFCH2CH(-O-)CH2 (3a-3c) in yields of 94-96% (total yields of the two-step synthesis starting from RF-I were 85-87%). The chemoselectivity of the oxirane formation appeared to be very dependent on the solvent used. Dependence on the reaction conditions on formation of byproducts RFCH=CHCH2OAc (4a-4c) and RFCH=CHCH2OH (5a-5c) in the epoxidation reaction was studied.

Novel perfluoroalkylated derivatives of D-galactopyranose and xylitol for biomedical uses. Hemocompatibility and effect on perfluorocarbon emulsions

6-O-(4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxyheptyl)-, 6-O-(4,4,5,5,6,6,7,7, 8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, and 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,10, 10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-d-galactopyranose (9, 10, and 11, resp.) were prepared by a two-step synthesis including the reaction of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose with 2-[(perfluoroalkyl) methyl]oxiranes under catalysis with BF3·Et2O. Similarly, 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl) -dl-xylitol (18, 19, and 20, resp.) were prepared by a two-step synthesis from the corresponding 1,2:3,4-di-O-isopropylidene-dl-xylitol. Most of the both types of fluoroalkylated carbohydrate derivatives 9-11 and 18-20 generally displayed very low level of hemolytic activity and excellent co-emulsifying properties on testing on perfluorodecalin-Pluronic F-68 microemulsions.

Mixed fluoroalkyl-alkyl surfactants

A surfactant of formula 1 [in-line-formulae](Rf-A)a-Q-([B]k—R)b??Formula 1[/in-line-formulae] wherein a and b are each independently 1 or 2;Rf is a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen;R is a C1 to C20 linear, branched or cyclic alkyl, or a C6 to C10 aryl;B is —(CH2CHR1O)x—,k is 0 or 1, x is 1 to about 20,A is —(CH2)m[(CHR1CH2O)]s—[(CH2)m(CH)tCHOH(CH2)m]e—, wherein each m is independently 0 to 3, s is 0 to about 30, t is 0 or 1, and e is 0 or 1,R1 is H or CH3,Q is: —OP(O)(O?M+)(O)—,—O—,—S—(CH2)m—C(O)—O—,—SO2—O——CH2CH2O—C(O)CH2C(OH)(V)CH2C(O)O—;—(CH2CH2O)xCH2CH(OH)—(CH2CH2O)x—(CH2)m—Si[OSi(R2)3]2—, —SO2NR2—,—(CH2CH2O)zC(O)CH(SO3?M+)CH2C(O)(OCH2CH2)z—wherein z is 1 to about 15, or a bond when s is a positive integer,V is —C(O)OR3 and R3 is H, CH3 or Rf;R2 is C1 to C4 alkyl, andM+ is a Group 1 metal or an ammonium (NHxR2y)+ cation wherein x+y=4, and R2 is C1 to C4 alkyl,provided that when Q is —OP(O)(O?M+)(O)— or when Q is —(CH2CH2O)z—C(O)CH(SO3?M+)CH2C(O)(OCH2CH2)z—, then at least one of s or e is a positive integer.

Fluorine-containing polyfunctional (meth) acrylate composition low refractivity material and reflection reducing film

PCT No. PCT/JP97/01952 Sec. 371 Date Feb. 9, 1998 Sec. 102(e) Date Feb. 9, 1998 PCT Filed Jun. 9, 1997 PCT Pub. No. WO97/47585 PCT Pub. Date Dec. 18, 1997Fluorine-containing polyfunctional (meth)acrylate represented by the formula (1), as well as a composition, a low refractivity material and a reflection reducing film in which the (meth)acrylate is utilized: wherein X stands for a fluoroalkyl group of C1-14 having 3 or more F, or a fluorocycloalkyl group of C3-14 having 4 or more F; Y1, Y2, and Y3 stand for H, an acryloyl group or a methacryloyl group, and at least two of Y1, Y2, and Y3 stand for an acryloyl group or a methacryloyl group; Z stands for H or an alkyl group of C1-3; and n and m is an integer of 0 or 1, and n+m=1.

Synthesis and polymerization of novel fluorinated morpholino acrylates and methacrylates

The synthesis of four fluorinated acrylates and methacrylates bearing a morpholino group in the lateral chain was achieved in four steps in very high yield: the radical addition of perfluoroalkyl iodides on to allyl acetate followed by an alkaline cyclization led to fluorinated epoxides.These compounds reacted with an excess of morpholine and yielded morpholinofluorinated alcohols that, condensed with acrylic or methacrylic anhydride, produced the expected fluorinated acrylic or methacrylic monomers, respectively.The behaviour in homopolymerization of such new olefins involved the study of the square of the propagation rate constant to the termination rate constant ratio (k2p/kte) by two different methods.The poor reactivity of these monomers has been shown by a GC kinetic study and also by the calculation of the yield.The values of k2p/kte show that they are two-hundred-times less reactive than usual fluorinated acrylic monomers.We finally propose a reactivity scale for such fluorinated monomers. - Keywords: Monoaddition; Acrylic derivatives; Kinetics; Morpholinofluorinated compounds; NMR spectroscopy; Mass spectrometry

Copper-catalyzed addition of perfluoroalkyl iodides to unsaturated alcohols and transformation of the addition products

Iodoperfluoroalkyl alcohols RFCH2CHI(CR2)nOH (RF = C6F13; R = H, CH3; n = 1-3, 9) have been readily prepared in high yield by the addition of perfluoroalkyl iodides RFI to allylic and other unsaturated alcohols at 120 deg C in the presence of a catalytic amount (10percent mol) of metallic copper powder.The dibenzoyl peroxide-induced reaction gave lower yields of the addition products in most cases.The chemical changes of iodoperfluoroalkylated alcohols to epoxides and alcohols are described.A discussion of the by-products obtained and of the reaction mechanism is provided.

Addition of RFI (CnF2n+1I; n = 4, 6, 8) to allyl alcohol catalyzed by zinc in different solvents: application to the synthesis of F-alkyl epoxypropanes

The addition of RFI to allyl alcohol catalyzed by zinc in different solvents has been studied.The adduct RFCH2CHICH2OH readily gives the corresponding F-alkyl epoxypropane.