78560-45-9

Basic information

• Product Name: 1H,1H,2H,2H-PERFLUOROOCTYLTRICHLOROSILANE
• Synonyms: Silane, trichloro(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-;1H,1H,2H,2H-PERFLUOROOCTYLTRICHLOROSILANE;(TRIDECAFLUORO-1,1,2,2-TETRAHYDROOCTYL)TRICHLOROSILANE;(TRIDECAFLUORO-1,1,2,2-TETRAHYDROOCTYL)-1-TRICHLOROSILANE;TRICHLORO(1H,1H,2H,2H-PERCHLOROOCTYL)SILANE;TRICHLORO(1H,1H,2H,2H-PERFLUOROOCTYL)SILANE;Perfluorooctyltrichlorosilane;Trichloro(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane
• CAS NO: 78560-45-9
• Molecular Formula: C₈H₄Cl₃F₁₃Si
• Molecular Weight: 481.54
• EINECS: 278-947-6
• Mol File: 78560-45-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: -32°C
• Boiling Point: 192 °C(lit.)
• Flash Point: 189 °F
• Appearance: /
• Density: 1.3 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.486mmHg at 25°C
• Refractive Index: n20/D 1.352(lit.)
• Solubility: Miscible with tetrahydrofuran, tetrhydropyran, toluene and other
• Water Solubility: 580μg/L at 20℃
• Sensitive: Moisture Sensitive
• Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents, water, alcohols, bases.
• BRN: 6154526
• CAS DataBase Reference: 1H,1H,2H,2H-PERFLUOROOCTYLTRICHLOROSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H,2H,2H-PERFLUOROOCTYLTRICHLOROSILANE(78560-45-9)
• EPA Substance Registry System: 1H,1H,2H,2H-PERFLUOROOCTYLTRICHLOROSILANE(78560-45-9)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2987 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 78560-45-9(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

1H,1H,2H,2H-Perfluorooctyltrichlorosilane is used in the silanization of silicon wafer. Self assembled monolayers treated with this, acts as an anti adhesive layer and release of cured poly(dimethyl siloxanes). It is also used to fabricate chemical surface patterns of self assembled monolayers.

General Description

Trichloro(1H,1H,2H,2H-perfluorooctyl)silane (PFOCTS) is a chlorosilane that forms a self-assembled monolayer (SAM) on a variety of substrates. It is majorly used to modify the surface with superhydrophobic properties. It is a biocompatible polymer with low surface energy. PFOCTS exhibits anti-fouling properties with high wettability which facilitates the release of different composites from the mold.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H4Cl3F13Si/c9-25(10,11)2-1-3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)24/h1-2H2

Synthetic route

Pt(0)-divinyltetramethyidisiloxane + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) → (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9)

Conditions	Yield
With trichlorosilane In 5,5-dimethyl-1,3-cyclohexadiene	99%

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) → (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9)

Conditions	Yield
With dihydrogen hexachloroplatinate; trichlorosilane at 100℃; for 70h;	98%
With dihydrogen hexachloroplatinate; trichlorosilane In isopropyl alcohol at 100℃;	83%
With trichlorosilane; chloroplatinic acid 1,1,3,3-tetramethyl-1,3-divinyldisiloxane complex at 60℃; for 4h;	80%
With dihydrogen hexachloroplatinate; trichlorosilane In isopropyl alcohol at 100℃; for 18h;	79%
With trichlorosilane; platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane In xylene at 86 - 126℃; under 760.051 - 5625.56 Torr; for 4.5 - 10.5h; Product distribution / selectivity;	2.6%

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + trichlorosilane (10025-78-2) → (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9)

Conditions	Yield
platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In xylene at 110℃; under 18751.9 Torr; for 192h; Industry scale;

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → (1H,1H,2H,2H-tridecafluoro-octyl)trifluorosilane (157333-81-8)

Conditions	Yield
With hydrogen fluoride In ethanol at 0℃;	99%
With hydrogen fluoride In diethyl ether; ethanol Ambient temperature; Yield given;

1,3,5,7,9,11,14-heptaisobutyltricyclo[7.3.3.15,11]heptasiloxane-endo-3,7,14-triol (307531-92-6) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → heptaisobutyl(tridecafluoro-1,1,2,2-tetrahydrooctyl)-T8-silsesquioxane

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	98%

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) + 1,3,5,7,9,11,14-heptacyclopentyltricyclo[7.3.3.15,11]heptasiloxane-endo-3,7,14-triol (183387-28-2) → heptacyclopentyl(3,3,3-tridecafluoro-1,1,2,2-tetrahydrooctyl)-T8-silsesquioxane

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.416667h; Inert atmosphere;	92%

C10H10F8O3 (66818-53-9) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → C38H31F37O9Si

Conditions	Yield
at 0℃; for 7h; Inert atmosphere; Neat (no solvent);	90%

allyl bromide (106-95-6) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → 1H,1H,2H,2H-perfluorooctyltriallylsilane (193828-95-4)

Conditions	Yield
Stage #1: allyl bromide With magnesium In diethyl ether at 0 - 5℃; for 2h; Stage #2: (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane In diethyl ether for 24h; Heating;	82%

hepta(3,3,3-trifluoropropyl)tricycloheptasiloxane trisodium silanolate + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → tridecafluoro-1,1,2,2-tetrahydrooctylhepta(3,3,3-trifluoropropyl)-T8-silsesquioxane (1003025-04-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 3h;	82%
With triethylamine In tetrahydrofuran Inert atmosphere;

sodium methylate (124-41-4) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → (1H,1H,2H,2H-tridecafluorooctyl)trimethoxysilane

Conditions	Yield
In methanol; 1,1,2-Trichloro-1,2,2-trifluoroethane for 1h; Ambient temperature;	70.9%

silver cyanate (3315-16-0) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → C11H4F13N3O3Si

Conditions	Yield
In benzene Heating;	58%

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl magnesium iodide (76598-01-1) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → tris(tridecafluoro-octyl)chlorosilane

Conditions	Yield
In diethyl ether for 18h; Heating;	27%

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) + 1-bromo-4-(trifluorovinyloxy)benzene (134151-77-2) → chloro-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-bis-(4-trifluorovinyloxy-phenyl)-silane

Conditions	Yield
Stage #1: 1-bromo-4-(trifluorovinyloxy)benzene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 1h; Stage #2: (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane In diethyl ether; pentane at -78℃; for 24h;

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → 3-[bis-(3-hydroxy-propyl)-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-silanyl]-propan-1-ol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Mg / diethyl ether / 2 h / 0 - 5 °C 1.2: 82 percent / diethyl ether / 24 h / Heating 2.1: BH3 / tetrahydrofuran / 3 h / 20 °C 2.2: 76 percent / aq. NaOH; H2O2 / tetrahydrofuran / 2 h / 20 °C View Scheme

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → 3-[bis-(2,3-dihydroxy-propyl)-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-silanyl]-propane-1,2-diol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Mg / diethyl ether / 2 h / 0 - 5 °C 1.2: 82 percent / diethyl ether / 24 h / Heating 2.1: 67 percent / NMNO*H2O; aq. osmium tetraoxide / acetone / 20 °C View Scheme

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → tris(tridecafluoro-octyl)fluorosilane

Conditions	Yield
Multi-step reaction with 2 steps 1: 27 percent / diethyl ether / 18 h / Heating 2: 40percent HF / diethyl ether / Ambient temperature View Scheme

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → tris(tridecafluoro-octyl)trifluoropropylsilane

Conditions	Yield
Multi-step reaction with 3 steps 1: 27 percent / diethyl ether / 18 h / Heating 2: 40percent HF / diethyl ether / Ambient temperature 3: 58 percent / diethyl ether / 1.) -33 deg C, 5 h, 2.) RT, 3 d View Scheme

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → C26H43F13O12Si (887651-67-4)

Conditions	Yield
at 150℃; under 15.0015 - 37.5038 Torr; for 2.5h;

isopropyllithium (1888-75-1) + (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) + trimethylsilylacetylene (1066-54-2) → C19H27F13Si2

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane for 1h; Cooling with ice bath; Stage #2: (tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane In tetrahydrofuran; hexane for 5.75h; Stage #3: isopropyllithium With ammonium chloride In tetrahydrofuran; hexane; water; pentane at 0 - 20℃;

(tridecafluoro-1,1,2,2-tetrahydrooctyl)trichlorosilane (78560-45-9) → (tridecafluorooctyl)dichlorosilane + dimethylsilicon dichloride (75-78-5)

Conditions	Yield
With trihexyl(tetradecyl)phosphonium chloride; dimethylmonochlorosilane at 60 - 85℃; Inert atmosphere;

Upstream product

• 25291-17-2 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene 
• 10025-78-2 trichlorosilane 

Downstream Products

• 85857-16-5 (1H,1H,2H,2H-tridecafluorooctyl)trimethoxysilane 
• 102488-47-1 chlorodimethyl(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane 
• 75-78-5 dimethylsilicon dichloride 

Relevant articles and documents

Study of the alkylation of chlorosilanes. Part I. Synthesis of tetra(1H,1H,2H,2H-polyfluoroalkyl)silanes

The synthesis and structural characterization of tetra(1H,1H,2H,2H-polyfluoroalkyl)silanes with the same or different chain lengths CnF2n+1 linked to Si (1nG) is reported.When the synthesis was effected from chlorosilanes were obtained.The last fluorinated chain was introduced either via a fluoroalkyllithium reagent or by hydrosilylation of the trialkylsilanes.Some properties and characterization by 1H, 19F and 29Si NMR spectroscopy of the 1H,1H,2H,2H-polyfluoroalkylsilanes are described.

SPECIFIC PROCESS FOR PREPARING SILICON COMPOUNDS BEARING FLUOROALKYL GROUPS BY HYDROSILYLATION

The present invention relates to a process for preparing silicon compounds bearing fluoroalkyl groups by hydrosilylation of a fluoroolefin in the presence of a hydrosilylation catalyst, which comprises initially charging and heating a hydrogenchlorosilane, then metering in the fluoroolefin and reacting the reaction mixture and subsequently isolating the hydrosilylation product.

Process for preparing fluoroalkyl-containing organosilicon compounds, and their use

Fluoroalkyl organosilicon compounds are prepared by reacting fluoroolefins with organosilicon compounds that contain at least one H--Si group, in the presence of a Pt(0) complex catalyst. Further, fluoroalkylalkoxy organosilicon compounds are prepared by esterifying fluoroalkyl organosilicon compounds. The process proceeds uniformly under mild conditions with high yields and selectivities.