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27607-77-8

Basic Information
CAS No.: 27607-77-8
Name: Trimethylsilyl trifluoromethanesulfonate
Article Data: 47
Molecular Structure:
Molecular Structure of 27607-77-8 (Trimethylsilyl trifluoromethanesulfonate)
Formula: C4H9F3O3SSi
Molecular Weight: 222.26
Synonyms: Methanesulfonicacid, trifluoro-, trimethylsilyl ester (8CI,9CI);Silanol, trimethyl-, trifluoromethanesulfonate(8CI);Trifluoromethanesulfonic acid trimethylsilyl ester;Trimethylsilanoltrifluoromethanesulfonate;Trimethylsilyl triflate;Trimethylsilyl trifluoromethylsulfonate;Trimethylsilyl trifluoromethanesulfonate;
EINECS: 248-565-4
Density: 1.276 g/cm3
Melting Point: 25°C
Boiling Point: 140 °C at 760 mmHg
Flash Point: 38.5 °C
Solubility: reacts with water
Appearance: clear colourless to light brown fuming liquid
Hazard Symbols: CorrosiveC, FlammableF
Risk Codes: 10-14-34
Safety: 16-26-36/37/39-45-8
Transport Information: UN 2920 8/PG 2
PSA: 51.75000
LogP: 2.76830
Synthetic route
75-76-3

tetramethylsilane

1493-13-6

trifluorormethanesulfonic acid

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
for 1h; Ambient temperature;99%
43112-38-5

3-(trimethylsilyl)-2-oxazolidinone

1493-13-6

trifluorormethanesulfonic acid

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
at 40℃; for 0.25h;98%
for 0.0333333h;80%
75-77-4

chloro-trimethyl-silane

1493-13-6

trifluorormethanesulfonic acid

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
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;
1493-13-6

trifluorormethanesulfonic acid

18156-74-6

1-(Trimethylsilyl)imidazole

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
In diethyl ether at 10℃; for 1h;96%
99542-57-1

(dimethylsilyl)methyl trifluoromethanesulfonate

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
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;
18306-29-1

bis(trimethylsilyl)sulphate

2794-60-7

barium trifluoromethanesulfonate

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
at 140 - 150℃;95%

C16H42PSi4

2923-28-6

silver trifluoromethanesulfonate

A

27607-77-8

trimethylsilyl trifluoromethanesulfonate

B

C27H62AgF3O3P2SSi6

Conditions
ConditionsYield
In benzene-d6 Inert atmosphere;A 90%
B 92%
1066-40-6

Trimethylsilanol

358-23-6

trifluoromethylsulfonic anhydride

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: Trimethylsilanol; trifluoromethylsulfonic anhydride at 45℃; for 3.5h;
Stage #2: With chloro-trimethyl-silane at 15℃; for 2.5h; Temperature;
89%
107-46-0

Hexamethyldisiloxane

358-23-6

trifluoromethylsulfonic anhydride

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
at 70 - 75℃; for 2h;88%
5936-98-1

trichloromethyltrimethylsilane

1493-13-6

trifluorormethanesulfonic acid

27607-77-8

trimethylsilyl trifluoromethanesulfonate

Conditions
ConditionsYield
at 120℃; for 0.833333h;88%
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Specification

The IUPAC name of this chemical is trimethylsilyl trifluoromethanesulfonate. With the CAS registry number 27607-77-8, it is also named as Methanesulfonic acid, 1,1,1-trifluoro-, trimethylsilyl ester. The product's categories are 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. It is clear colourless to light brown fuming liquid which reacts violently with water. Additionally, this chemical should be stored at the temperature of 2-8 °C.

The other characteristics of Trimethylsilyl Trifluoromethanesulfonate can be summarized as: 
(1)ACD/LogP: 2.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.54; (4)ACD/LogD (pH 7.4): 2.54; (5)#H bond acceptors: 3; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 2; (8)Index of Refraction: 1.379; (9)Molar Refractivity: 40.23 cm3; (10)Molar Volume: 174 cm3; (11)Polarizability: 15.95×10-24 cm3; (12)Surface Tension: 21.9 dyne/cm; (13)Enthalpy of Vaporization: 36.17 kJ/mol; (14)Vapour Pressure: 7.81 mmHg at 25°C; (15)Rotatable Bond Count: 2; (16)Exact Mass: 221.999376; (17)MonoIsotopic Mass: 221.999376; (18)Topological Polar Surface Area: 51.8; (19)Heavy Atom Count: 12; (20)Complexity: 244.

Preparation of Trimethylsilyl Trifluoromethanesulfonate:
It can be obtained by hexamethyl-disiloxane and trifluoro-methanesulfonic acid anhydride. This reaction must react at temperature of 70-75°C for 2 hours. The yield is 88%.
Preparation of Trimethylsilyl Trifluoromethanesulfonate

Uses of Trimethylsilyl Trifluoromethanesulfonate:
It is cationic initiator which is used as catalysts and silicon reagent in organic synthesis. It also can react with 1,2-epoxy-cyclopentane to get (2-cyclopenten-1-yloxy)trimethylsilane. This reaction needs reagent DBU and solvent benzene.
Uses of Trimethylsilyl Trifluoromethanesulfonate

Safety information of Trimethylsilyl Trifluoromethanesulfonate:
When you are using this chemical, please be cautious about it as the following:It is flammable, so people should keep it away from sources of ignition. And it can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure. 
1. SMILES:C[Si](C)(C)OS(=O)(=O)C(F)(F)F
2. InChI:InChI=1/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
3. InChIKey:FTVLMFQEYACZNP-UHFFFAOYAR