27607-77-8

Basic information

• Product Name: Trimethylsilyl trifluoromethanesulfonate
• Synonyms: SILANE TMS-TRIFLATE;TMSOTF;TMS TRIFLATE;TRIMETHYLSILYL TRIFLATE;TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE;TRIMETHYLSILYL TRIFLUOROMETHANESULPHONATE;TRIMETHYLSILYL TRIFLUOROMETHYLSULFONATE;TRIMETHYLSILYL TRIFLUOROMETHYLSULPHONATE
• CAS NO: 27607-77-8
• Molecular Formula: C₄H₉F₃O₃SSi
• Molecular Weight: 222.2581696
• EINECS: 248-565-4
• Product Categories: straight chain compounds;Small molecule;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Silyl Esters;Si-O Compounds;Synthetic Organic Chemistry;metal triflate compounds;Cationic initiator
• Mol File: 27607-77-8.mol
• Article Data: 47

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 77 °C80 mm Hg(lit.)
• Flash Point: 78 °F
• Appearance: Clear colorless to light brown/Fuming Liquid
• Density: 1.228 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.22E-09mmHg at 25°C
• Refractive Index: n20/D 1.36(lit.)
• Storage Temp.: 2-8°C
• Solubility: sol aliphatic and aromatic hydrocarbons, haloalkanes, ethers.
• Water Solubility: REACTS
• Sensitive: Moisture Sensitive
• Merck: 14,9719
• BRN: 1868911
• CAS DataBase Reference: Trimethylsilyl trifluoromethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylsilyl trifluoromethanesulfonate(27607-77-8)
• EPA Substance Registry System: Trimethylsilyl trifluoromethanesulfonate(27607-77-8)

Safety Data

• Hazard Codes: C,F
• Statements: 10-14-34
• Safety Statements: 16-26-36/37/39-45-8
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 27607-77-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light brown fuming liquid

Physical properties

bp 45–47 °C/17 mmHg, 39–40 °C/12 mmHg; d 1.225 g cm?3.

Uses

Trimethylsilyl Trifluoromethane?sulfonate is generally used following reactions:1. Silylation. TMSOTf is widely used in the conversion of car?bonyl compounds to their enol ethers. The conversion is some 109 faster with TMSOTf/triethylamine than with chlorotrimethy?lsilane.Dicarbonyl compounds are converted to the corresponding bis?enol ethers; this method is an improvement over the previous two?step method.In general, TMSOTf has a tendency toC-silylation which is seen most clearly in the reaction of esters, whereC-silylation dominates over O-silylation.2.Carbonyl Activation. 1,3-Dioxolanation of conjugated enals is facilitated by TMSOTf in the presence of 1,2-bis(trimethylsilyl?oxy)ethane. In particular, highly selective protection of sterically differentiated ketones is possible (eq 10).TMSOTf mediates a stereoselective aldol-type condensation of silyl enol ethers and acetals (or orthoesters). The nonbasic reaction conditions are extremely mild. The use of TMSOTf in aldol reactions of silyl enol ethers and ketene acetals with aldehydes is ubiquitous. Stereoselective cyclization of α,β-unsaturated enamide esters is induced by TMSOTf and has been used as a route to quinolizidines and indolizidines.3.The often difficult conjugate addition of alkynyl organometallic reagents to enones is greatly facilitated by TMSOTf. In particular, alkynyl zinc reagents (normally unreactive with α,β-unsaturated carbonyl compounds) add in good yield.The formation of nitrones by reaction of aldehydes and ketones with N-methyl-N,O-bis(trimethylsilyl)hydroxylamine is accelerated when TMSOTf is used as a catalyst; the acceleration is particularly pronounced when the carbonyl group is under a strong electronic influence.5. Methyl glucopyranosides and glycopyranosyl chlorides undergo allylation with allylsilanes under TMSOTf catalysis to give predominantly α-allylated carbohydrate analogs.Glycosidation is a reaction of massive importance and wide?spread employment. TMSOTf activates many selective glycosidation reactions.4.O-Silylation. The formation of TMS ethers can be achieved by reacting the requisite alcohol with TMSOTf and an amine (triethy?lamine, pyridine, or 2,6-lutidine) in dichloromethane;C-Silylation. Depending on the reaction conditions, sec?ondary amides can be either C-silylated or N-silylated;N-Silylation. The N-bis-silylation of α-amino acids with TMSOTf is only effective for glycine; for other α-amino acids N-mono-silylation prevails because the larger size of the carbon chain at the α-position hinders bis-silylation;C,O-Bis-silylation. Bis-silylation ofα,β-unsaturated carbonyl compounds can be achieved by palladium-TMSOTf-catalyzed addition of disilanes to enones, enals, or aromatic aldehydes via an η3-silyloxyallylpalladium intermediate;Carbonyl Activation. TMSOTf frequently acts as a Lewis acid and it is able to activate several functional groups (the car?bonyl group, the acetal unit, the nitrone moiety,…) thus facilitating different kinds of reactions;Acetal Activation. TMSOTf acts as a catalyst for the addi?tion of several nucleophiles (allylsilanes, allylstannanes, silyl enol ethers, trimethylsilyl cyanide) towardN,O-acetals;Nitrone Activation. The nucleophilic addition to aldonitrones depends on the nature of the metal involved and the presence/absence of an activator;Epoxide Ring Opening. One-pot alkylation-O-silylation re?actions of epoxides take place in excellent yields;Cleavage of Protecting Groups. THP ethers of primary, sec?ondary, and phenolic alcohols can be conveniently deprotected at room temperature; Hypervalent Iodine Chemistry. The formation of hyperva?lent iodine complexes is often promoted by TMSOTf.

Uses

Trimethylsilyl Trifluoromethanesulfonate is a trialkylsilyl triflate used as a catalyst in organic synthesis. Trimethylsilyl Trifluoromethanesulfonate is used in combination with boron trifluoride eth yl ether to prepare a Lewis acid that is more powerful than its components and especially effective in acetonitrile solvent. Trimethylsilyl is a common reagent used in a Dieckmann-like cyclization of ester-imides and diesters.

Uses

Catalyst and silylating agent for organic syntheses.

InChI:InChI=1/C18H3F35O6/c19-2(1-54,8(26,27)28)55-15(46,47)4(22,10(32,33)34)57-17(50,51)6(24,12(38,39)40)59-18(52,53)7(25,13(41,42)43)58-16(48,49)5(23,11(35,36)37)56-14(44,45)3(20,21)9(29,30)31/h54H,1H2

Synthetic route

tetramethylsilane (75-76-3) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
for 1h; Ambient temperature;	99%

3-(trimethylsilyl)-2-oxazolidinone (43112-38-5) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at 40℃; for 0.25h;	98%
for 0.0333333h;	80%

chloro-trimethyl-silane (75-77-4) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
In n-heptane at 50 - 60℃; for 13h; Large scale;	96.55%
for 7h; Heating; Yield given;
at 20℃;
at 40℃; for 24h; Schlenk technique; Inert atmosphere;

trifluorormethanesulfonic acid (1493-13-6) + 1-(Trimethylsilyl)imidazole (18156-74-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
In diethyl ether at 10℃; for 1h;	96%

(dimethylsilyl)methyl trifluoromethanesulfonate (99542-57-1) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at 80℃; for 9h;	95%
In benzene-d6 at 135℃; Rate constant; Mechanism; τ1/2;
In neat (no solvent) at 134.9℃; Rate constant; Thermodynamic data; lgA, EA, ΔH(excit.), ΔS(excit.), ΔG(excit.), ΔrH;
at 80℃; Kinetics; Rate constant;

bis(trimethylsilyl)sulphate (18306-29-1) + barium trifluoromethanesulfonate (2794-60-7) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at 140 - 150℃;	95%

C16H42PSi4 + silver trifluoromethanesulfonate (2923-28-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + C27H62AgF3O3P2SSi6

Conditions	Yield
In benzene-d6 Inert atmosphere;	A 90% B 92%

Trimethylsilanol (1066-40-6) + trifluoromethylsulfonic anhydride (358-23-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
Stage #1: Trimethylsilanol; trifluoromethylsulfonic anhydride at 45℃; for 3.5h; Stage #2: With chloro-trimethyl-silane at 15℃; for 2.5h; Temperature;	89%

Hexamethyldisiloxane (107-46-0) + trifluoromethylsulfonic anhydride (358-23-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at 70 - 75℃; for 2h;	88%

trichloromethyltrimethylsilane (5936-98-1) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at 120℃; for 0.833333h;	88%

trifluorormethanesulfonic acid (1493-13-6) + allyl-trimethyl-silane (762-72-1) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	85%
In dichloromethane at 0℃; for 2h;

Trimethylsilanol (1066-40-6) + trifluoromethane sulfonyl chloride (421-83-0) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at 15℃; for 4h; Temperature;	80%

2-(trimethylsilyl)propene (18163-07-0) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + t-butyldimethylsiyl triflate (69739-34-0)

Conditions	Yield
In pentane at 0℃; for 0.166667h; Yield given;	A n/a B 66%
In pentane at 0℃; for 0.166667h; Yields of byproduct given;	A n/a B 66%

trifluorormethanesulfonic acid (1493-13-6) + (trifluoromethyl)trimethylsilane (81290-20-2) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
With boron tribromide at -25 - 20℃;	54%

trifluorormethanesulfonic acid (1493-13-6) + (Z)-trimethylsilyl N-trimethylsilylacetimidate (10416-59-8, 132255-83-5) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
for 0.0833333h;	43%

trifluorormethanesulfonic acid (1493-13-6) + trimethylsilyl trichloroacetate (25436-07-1) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
for 0.0833333h;	40%

trifluorormethanesulfonic acid (1493-13-6) + monotrimethylsilylacetamide → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
for 0.0833333h;	35%

chloro-trimethyl-silane (75-77-4) + Chlorine(I) trifluoromethanesulfonate (65597-24-2) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
at -111 - 0℃;

trifluoromethylsulfonic anhydride (358-23-6) + methyl trimethylsilyl tert-butylphosphonate (97730-10-4) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + O-methyl-tert-butylphosphonic trifluoromethanesulfonic anhydride (97730-01-3)

Conditions	Yield
In dichloromethane for 12h; Ambient temperature;

N,N,N'-tris(trimethylsilyl)phosphenimidous amide (50732-21-3, 65428-75-3) + bis(diisopropylamino)phosphanylium trifluoromethanesulfonate (114684-87-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + N,N,N',N'-tetraisopropyl-1,3-bis(trimethylsilanyl)[1,3,2,4]diazadiphosphetidine-2,4-diamine (65160-85-2, 66435-33-4)

Conditions	Yield
Yield given. Multistep reaction;

N,N,N'-tris(trimethylsilyl)phosphenimidous amide (50732-21-3, 65428-75-3) + bis(diethylamino) phosphenium triflate → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + N,N,N',N'-Tetraethyl-1,3-bis-trimethylsilanyl-[1,3,2,4]diazadiphosphetidine-2,4-diamine (66435-31-2, 66435-32-3, 344867-26-1)

Conditions	Yield
Yield given. Multistep reaction;

μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine] (88016-29-9) + 4,4-dimethyl-1-(trimethylsilyl)-2-pentyne (84140-30-7) → t-butylallene (26981-77-1) + Hexamethyldisiloxane (107-46-0) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 4,4-dimethyl-1-(2-iodophenyl)-2-pentyne (131251-47-3)

Conditions	Yield
In dichloromethane-d2 at -80℃; Mechanism; or tributylstannyl compound;

trimethyl(trimethylstannyl)silane (16393-88-7) → trimethylsilyl trifluoromethanesulfonate (27607-77-8)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at -78℃;

C14H26NSi2(1+)*CF3O3S(1-) → trimethylsilyl fluoride (420-56-4) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) + C11H17NSi

Conditions	Yield
With cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide

C14H23F3O4PSSi(1+)*CF3O3S(1-) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + tert-butylphenylphosphinic trifluoromethanesulfonic anhydride (97730-00-2)

Conditions	Yield
In dichloromethane at 20℃;

trifluorormethanesulfonic acid (1493-13-6) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + ethylbenzene (100-41-4) + 1,1-Bis(triflyloxy)ethylbenzene

Conditions	Yield
With HW(CO)3(C5H5) In dichloromethane-d2 at 22℃; for 0.833333h; Product distribution; other times; without Cp(CO)3WH;	A 91 % Spectr. B 85 % Spectr. C 13 % Spectr.

trifluorormethanesulfonic acid (1493-13-6) + Bis(trimethylsilyl)ethyne (14630-40-1) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + acetylene (74-86-2)

Conditions	Yield
With HW(CO)3(C5H5) In dichloromethane-d2 at 22℃; for 0.5h; Product distribution;	A 100 % Spectr. B 48 % Spectr.

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2S,4aS,8aR)-5-(2-furan-3-yl-ethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-yloxy]-5-hydroxy-tetrahydro-pyran-4-yl ester (115243-86-2, 115269-43-7, 115269-44-8, 115269-45-9, 120056-50-0, 120056-51-1) → baiyunyl 2-O-trimethylsilyl-3,4,6-tri-O-acetyl-α-D-glucopyranoside (115243-90-8, 141978-30-5, 141978-31-6, 141978-32-7)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane for 10h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (E)-6-((tert-butyldimethylsilyl)oxy)hex-3-en-2-one (96429-43-5) → (E)-6-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanyloxy-hexa-1,3-diene (116072-20-9)

Conditions	Yield
With triethylamine In diethyl ether for 0.666667h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (22E,24R)-3α,5-Cyclo-5α-ergost-7,22-dien-6-one (3152-46-3, 80779-43-7, 116405-08-4) → (22E,24R)-6-Trimethylsiloxy-3α,5-cyclo-5α-ergost-6,22-diene (124696-42-0)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.333333h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1,9-dideoxyforskolin (64657-18-7) → 7β-acetoxy-8,13-epoxy-6β-trimethylsilanyloxy-labd-14-en-11-one (111455-15-3)

Conditions	Yield
With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 72h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-(phenylsulfinyl)hexan-2-one (141407-33-2) → Trimethyl-{(E)-1-[1-phenylsulfanyl-meth-(E)-ylidene]-pent-2-enyloxy}-silane (141407-36-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Mechanism; Ambient temperature; other β-keto sulfoxides;	100%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-Benzenesulfinyl-decan-2-one (141407-34-3) → Trimethyl-{(E)-1-[1-phenylsulfanyl-meth-(E)-ylidene]-non-2-enyloxy}-silane (141420-65-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-Benzenesulfinyl-4-(4-methoxy-phenyl)-butan-2-one (141407-35-4) → {(E)-3-(4-Methoxy-phenyl)-1-[1-phenylsulfanyl-meth-(E)-ylidene]-allyloxy}-trimethyl-silane (141407-37-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 4-(benzoyloxy)-1-(α-furyl)-1-methoxy-1-buten-3-one → (3Z)-4-(benzoyloxy)-1-(α-furyl)-1-methoxy-3-<(trimethylsilyl)oxy>-1,3-butadiene (102650-39-5)

Conditions	Yield
With triethylamine In diethyl ether 1.) -78 deg C, 10 min; 2.) room temp., 0.5 h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 2,2-dimethyl-6-cycloundecene-4,8-diyn-1-one (153093-79-9) → <(2,2-dimethyl-6,10-cycloundecdiene-4,8-diyn-1-yl)oxy>trimethylsilane (153093-81-3)

Conditions	Yield
With TEA In dichloromethane for 5h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + bis(p-dimethylaminophenyl)methanone (90-94-8) → methylen>(trimethylsilyl)oxonium-trifluormethansulfonat (80239-31-2)

Conditions	Yield
In dichloromethane at 15℃;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (E)-2-(4-oxopent-2-en-1-yl)isoindoline-1,3-dione (160072-66-2) → 2-((E)-4-Trimethylsilanyloxy-penta-2,4-dienyl)-isoindole-1,3-dione (160072-67-3)

Conditions	Yield
With triethylamine In benzene for 15h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + <1R-<1α(R*),3aβ,4α,7aα>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α,7a-dimethyloctahydro-1H-inden-1-acetaladehyde → <1R-(1α,3aβ,4α,7aα)>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7a-methyl-1-<1-methyl-2-<(trimethylsilyl)oxy>-1-ethenyl>octahydro-1H-indene

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 1h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-methylcyclohexan-4-one (589-92-4) → 4-methyl-1-(trimethylsilyloxy)-1-cyclohexene (38671-78-2)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1.5h;	100%
With triethylamine In dichloromethane for 1h;

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester (185810-98-4) → (1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester (185811-02-3)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane for 4h; Ambient temperature;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + methyl (phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranosid)uronate (225640-45-9) → methyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate (225640-47-1)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at -10℃; for 0.0833333h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + benzyl (phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranosid)uronate (225640-46-0) → benzyl (phenyl 2,3-di-O-benzyl-1-thio-4-O-trimethylsilyl-β-D-galactopyranosid)uronate (225640-48-2)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at -10℃; for 0.166667h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + Ethyl 2-methyl-3,3,3-trifluoropropionate (56354-75-7, 121773-36-2) → ((Z)-1-Ethoxy-3,3,3-trifluoro-2-methyl-propenyloxy)-trimethyl-silane

Conditions	Yield
With triethylamine at 100℃; for 5h; Substitution;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-ethoxycarbonyl-2-trimethylsilylaziridine (97042-79-0) → Ethyl N-(2-trifluoromethanesulfonyl-2-trimethylsilylethyl)carbamate

Conditions	Yield
Ring cleavage; Substitution;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 2-Methoxycarbonyl-2-dimethylphenylsilyl-1-phenylaziridine (265093-28-5) → 2-Methoxycarbonyl-2-dimethylphenylsilyl-1-phenyl-1-trimethylsilylaziridinium trifluoromethanesulfonate

Conditions	Yield
Salt formation;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 6-{[4-(tert-butyl-dimethyl-silanyloxy)-6-(4-iodo-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-2-[4-(tert-butyl-dimethyl-silanyloxy)-2-methylene-octa-5,7-dienyl]-5-methyl-tetrahydro-pyran-3,4-diol → C51H103IO8Si5

Conditions	Yield
With 2,6-dimethylpyridine In tetrahydrofuran at -78 - 0℃;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 2-(diphenylphosphinyl)-2'-(diphenylphosphanyl)-1,1'-binaphthalene (204862-91-9, 152646-80-5, 183244-55-5) → C47H41OP2Si(1+)*CF3O3S(1-)

Conditions	Yield
at 20℃;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + methoxybenzene (100-66-3) + 1,1-diphenyl-3-(trimethylsilyl)-1-(trimethylsilyloxy)prop-2-yne (350693-36-6) → (1-(4-methoxyphenyl)-3,3-diphenylpropa-1,2-dien-1-yl)trimethylsilane

Conditions	Yield
In dichloromethane at -78℃; for 3h; Friedel-Crafts reaction;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-fluoro-1-isopropyl-1-phenyl-3,3-bis-trifluoromethyl-2-oxa-1λ5-phospha-indan (434321-76-3) → Trifluoro-methanesulfonate1-isopropyl-1-phenyl-3,3-bis-trifluoromethyl-2-oxa-1-phosphonia-indan;

Conditions	Yield
In diethyl ether at 20℃;	100%
In diethyl ether at 20℃; for 0.333333h;

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-ethylsulfanyl-1-fluoro-3,3-bis-trifluoromethyl-1-(2,4,6-triisopropyl-phenyl)-2-oxa-1λ5-phospha-indan (434321-65-0) → Trifluoro-methanesulfonate1-ethylsulfanyl-3,3-bis-trifluoromethyl-1-(2,4,6-triisopropyl-phenyl)-2-oxa-1-phosphonia-indan;

Conditions	Yield
In diethyl ether at 20℃;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-2-(toluene-4-sulfonyl)-3,4,4a,8a-tetrahydro-2H,5H-isoquinoline-1,6-dione (447408-34-6) → 8a-allyl-4-(tert-butyl-diphenyl-silanyloxy)-2-(toluene-4-sulfonyl)-6-trimethylsilanyloxy-3,4,4a,8a-tetrahydro-2H-isoquinolin-1-one (447408-36-8)

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + C13H20N2OSi → Ditriflatobis[N-(isopropylideneimino)-benzimidato-N,O]silicon(IV)

Conditions	Yield
With tetrachlorosilane In dichloromethane; chloroform	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1-(2,2-dimethoxyethyl)-4-phenylcyclohexanol (779349-32-5) → (4-phenyl-1-(trimethylsiloxy)cyclohexyl)acetaldehyde

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.5h;	100%
Stage #1: trimethylsilyl trifluoromethanesulfonate; 1-(2,2-dimethoxyethyl)-4-phenylcyclohexanol With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.5h; Stage #2: With water In dichloromethane	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + C22H34O8 (807616-75-7) → C25H42O8Si (807617-20-5)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at -78℃; for 1h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (3S,4S)-4-Acetyl-3-methoxy-1-(4-methoxy-phenyl)-azetidin-2-one (812681-73-5) → (3S,4S)-3-Methoxy-1-(4-methoxy-phenyl)-4-(1-trimethylsilanyloxy-vinyl)-azetidin-2-one (804563-07-3)

Conditions	Yield
With triethylamine In dichloromethane at -78 - 20℃; for 2h;	100%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (-)-(1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate (767319-38-0) → Isobutyric acid (Z)-(2S,3R,4S)-1-eth-(Z)-ylidene-2,4-dimethyl-3-((S)-1-phenyl-ethoxy)-5-trimethylsilanyloxy-hept-5-enyl ester (847758-56-9)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane at -20 - 20℃; for 2h;

Upstream product

• 27607-63-2 5-Ethyl-4-methyl-3-heptanone 
• 27607-61-0 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluorononanesulphonyl chloride 
• 27607-42-7 2-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)amino]ethanol 
• 27607-36-9 2,2'-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)imino]bisethanol 
• 27607-33-6 CIS-1,2-CYCLOOCTANEDIOL 
• 27607-29-0 1-(DiMethylaMino)-2-propanol N-Oxide 
• 2760-64-7 CYCLOHEXYL 2,4-DIMETHYLPHENYL KETONE 
• 27606-27-5 2-allyl-2-(hydroxymethyl)propane-1,3-diol 
• 27606-09-3 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d]-1,3-dioxin 
• 27605-76-1 Oryzaemate 
• 27605-35-2 1-(tributylstannyl)-1H-imidazole 
• 2760-35-2 N-(4-BROMOPHENYL)PROPIONAMIDE 
• 2760-34-1 N-(naphthalen-2-yl)propanamide 
• 2760-33-0 N-(3-chlorophenyl)propanamide 

Downstream Products

• 157843-41-9 2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside 

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