14548-74-4

Basic information

• Product Name: 1H,1H-2,5-DI(TRIFLUOROMETHYL)-3,6-DIOXAUNDECAFLUORONONANOL
• Synonyms: 1H,1H-PERFLUORO(2,5-DIMETHYL-3,6-DIOXANONAN-1-OL);1H,1H-2,5-BIS(TRIFLUOROMETHYL)-3,6-DIOXAPERFLUORONONANOL;1H,1H-2,5-BIS(TRIFLUOROMETHYL)-3,6-DIOXAUNDECAFLUORONONANOL;1H,1H-2,5-DI(TRIFLUOROMETHYL)-3,6-DIOXAUNDECAFLUORONONANOL;1H,1H-2,5-di(Trifluoromethyl)-3,6-dioxa undeacafluoro nonanol;1H,1H-2,5-Di(trifluoromethyl)-3,6-;1H,1H-Heptadecafluoro(2,5-dimethyl-3,6-dioxanonan-1-ol);1H,1H-Perfluoro(2,5-methyl-3,6-dioxanonan-1-ol)
• CAS NO: 14548-74-4
• Molecular Formula: C₉H₃F₁₇O₃
• Molecular Weight: 482.09
• Mol File: 14548-74-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 155-156°C
• Flash Point: 123 °C
• Appearance: /
• Density: 1.719 g/cm³
• Vapor Pressure: 0.00313mmHg at 25°C
• Refractive Index: 1.292
• PKA: 12.56±0.10(Predicted)
• CAS DataBase Reference: 1H,1H-2,5-DI(TRIFLUOROMETHYL)-3,6-DIOXAUNDECAFLUORONONANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H-2,5-DI(TRIFLUOROMETHYL)-3,6-DIOXAUNDECAFLUORONONANOL(14548-74-4)
• EPA Substance Registry System: 1H,1H-2,5-DI(TRIFLUOROMETHYL)-3,6-DIOXAUNDECAFLUORONONANOL(14548-74-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 14548-74-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H3F17O3/c10-2(1-27,5(14,15)16)28-9(25,26)4(13,7(20,21)22)29-8(23,24)3(11,12)6(17,18)19/h27H,1H2

Synthetic route

perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride (2641-34-1) → 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 2h; Inert atmosphere; Reflux;	90%
Multi-step reaction with 2 steps 1: 86.3 percent / Na2CO3; MgSO4; silica gel / diethyl ether / 20 °C 2: 81.1 percent / NaBH4 / diethyl ether; methanol / 12 h / Heating View Scheme

methyl 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonanoate (26131-32-8) → 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4)

Conditions	Yield
With sodium tetrahydroborate In methanol; diethyl ether for 12h; Heating;	81.1%
With sodium tetrahydroborate In methanol; diethyl ether for 11h; Reflux; Inert atmosphere;	75%
With sodium tetrahydroborate; isopropyl alcohol
With sodium tetrahydroborate In methanol at 20℃; for 2h; Cooling with ice;

2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonyl trifluoromethanesulfonate (1173110-39-8) → 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4)

Conditions	Yield
With sodium hydride; phenol In dimethyl sulfoxide at 130℃; Inert atmosphere;

2,3,4,5,6-pentafluorostyrene (653-34-9) + 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C17H5F21O3

Conditions	Yield
Stage #1: 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]propan-1-ol With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 2,3,4,5,6-pentafluorostyrene In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;	90%

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) + 2-(trifluoromethyl)acrylic chloride (90715-73-4) → 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy]propyl 2-(trifluoromethyl)acrylate

Conditions	Yield
Stage #1: 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]propan-1-ol With pyridine at -10℃; for 0.333333h; Inert atmosphere; Stage #2: 2-(trifluoromethyl)acrylic chloride at -10 - 20℃; for 17h; Inert atmosphere;	85%

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) + Methacryloyl chloride (920-46-7) → 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonyl methacrylate

Conditions	Yield
With 2,2-diphenyl-1-picrylhydrazyl; triethylamine In diethyl ether at 20℃; for 4h;	82%

3-Bromopropionic acid (590-92-1) + 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C12H6BrF17O4 (820958-27-8)

Conditions	Yield
With trifluoroacetic anhydride at 20 - 30℃; for 4.5h;	80%

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) + 1-Adamantanecarbonyl chloride (2094-72-6) → C20H17F17O4 (709615-35-0)

Conditions	Yield
With pyridine at 20 - 50℃; for 5h;	74.4%
With pyridine at 25 - 50℃; for 5h;	74.4 %Spectr.

trifluoromethylsulfonic anhydride (358-23-6) + 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonyl trifluoromethanesulfonate (1173110-39-8)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	70.2%
With pyridine In dichloromethane Inert atmosphere;	70%

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C9H2Cl2F17O4P (1429405-66-2)

Conditions	Yield
With lithium chloride; trichlorophosphate	63%

vinyl acetate (108-05-4) + 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → 1,1-Dihydro-2,5-bis(trifluoromethyl)-3,6-dioxa-2,4,4,5,7,7,8,8,9,9,9,-undecafluorononyl vinyl ether

Conditions	Yield
With sulfuric acid; mercury(II) diacetate at 0 - 10℃; for 8h;	30%

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → 1,1-Dihydro-2,5-bis(trifluoromethyl)-3,6-dioxa-2,4,4,5,7,7,8,8,9,9,9,-undecafluorononyl 1,2-dichloroethyl ether (156731-88-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / mercuric acetate, conc. H2SO4 / 8 h / 0 - 10 °C 2: 88 percent / Cl2 / 10 - 15 °C View Scheme

Nonafluorobutanesulfonyl fluoride (375-72-4) + 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C13H2F26O5S (1357369-86-8)

Conditions	Yield
Stage #1: 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]propan-1-ol With sodium hydride Stage #2: Nonafluorobutanesulfonyl fluoride

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → 1-[2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonyl]imidazole (1173110-41-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride 2: acetonitrile / 10 h / Reflux; Inert atmosphere View Scheme

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → 1,3-bis[2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonyl]imidazolium nonafluorobutanesulfonate (1357369-98-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride 2: sodium carbonate / 4.25 h / 63 - 70 °C / Microwave irradiation; Inert atmosphere; Neat (no solvent); sealed vial View Scheme
Multi-step reaction with 2 steps 1: sodium hydride 2: 3 h / 63 - 70 °C / Microwave irradiation; Inert atmosphere; Neat (no solvent); sealed vial View Scheme
Multi-step reaction with 3 steps 1: sodium hydride 2: acetonitrile / 10 h / Reflux; Inert atmosphere 3: 3 h / 63 - 70 °C / Microwave irradiation; Inert atmosphere; Neat (no solvent); sealed vial View Scheme

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C4F9O3S(1-)*C17H7F26N2O4(1+) (1357370-09-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride 2: 63 °C / Microwave irradiation; Neat (no solvent); Inert atmosphere; sealed vial View Scheme
Multi-step reaction with 3 steps 1: sodium hydride 2: acetonitrile / 10 h / Reflux; Inert atmosphere 3: 63 °C / Microwave irradiation; Neat (no solvent); Inert atmosphere; sealed vial View Scheme

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C4F9O3S(1-)*C19H7F30N2O5(1+) (1357370-13-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride 2: 63 °C / Microwave irradiation; Neat (no solvent); Inert atmosphere; sealed vial View Scheme
Multi-step reaction with 3 steps 1: sodium hydride 2: acetonitrile / 10 h / Reflux; Inert atmosphere 3: 63 °C / Microwave irradiation; Neat (no solvent); Inert atmosphere; sealed vial View Scheme

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonylazide (1173110-46-7)

Conditions	Yield
Stage #1: 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]propan-1-ol With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 2h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 50℃; for 48h;	127g

2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxy]-1-propanol (14548-74-4) → C15H8F17N3O4

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / 0 °C 1.2: 48 h / 50 °C 2.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 2 h / 20 °C View Scheme

Upstream product

• 26131-32-8 methyl 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonanoate 
• 2641-34-1 perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride 
• 1173110-39-8 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonyl trifluoromethanesulfonate 

Relevant articles and documents

HFPO trimer-based alkyl triflate, a novel building block for fluorous chemistry. Preparation, reactions and 19F gCOSY analysis

Triflate 4, CF3(CF2)2O-CF(CF 3)CF2O-CF(CF3)CH2-OTf (R FOCH2OTf), of the HFPO trimer-based alcohol 3 (R FOCH2OH) is a novel highly fluorinated building block for fluorous chemistry. In analogy to similar polyfluorinated triflates with methylene spacer, its reactivity is limited to strong and soft nucleophiles. Whereas reactions with cyanide anion, phenolate anion, enolate of diethyl malonate or lithium salt of benzaldehyde bis(phenylsulfanyl)acetal were unsuccessful, the corresponding imidazole 5, iodide 6 or azide 7 were prepared in good yields. Reaction of imidazole 5 with (perfluorohexyl)methyl triflate (9) afforded highly fluorinated non-crystalline imidazolium salt 8, TfO -RFOCH2-(C3H3N 2)+-CH2C6F13-n, which could be employed as fluorous ionic liquid or intermediate for fluorous carbenes. Complete assignment of complex 19F NMR spectra of all compounds employed was accomplished using 19F gCOSY NMR method.

A method for preparing the fluorine carbon is mellow and its application (by machine translation)

The invention discloses a method for preparing the fluorine carbon is mellow and its application, the preparation method is with hexafluoropropylene oxide as the raw material, in a suitable reaction temperature, and under the action of the solvent in the catalyst, the polymerization of the generated or nexaituoropropene dimer and trimer, with no need for separate directly converted into a methyl ester, obtained by rectification of dimer, trimer methyl ester, the fluorine carbon is mellow respectively reduction of dimer, trimer the fluorine carbon is mellow, finally again rectification, the purity is as high as 99.7%. (by machine translation)

2,4,4,5,7,7,8,8,9,9,9-Undecafluoro-2,5-bis(trifluoromethyl)-3, 6-dioxanonyl methacrylate

The title monomer (4) was prepared from the trimer of hexafluoropropene-1,2-oxide, 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)- 3,6-dioxanonanoyl fluoride (1), via methyl ester 2 that was reduced by sodium borohydride to the corresponding alkanol 3, which was finally acylated by methacryloyl chloride.