Basic information
- CAS
79271-56-0- Standard SMILES
CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F- InChIKey
STMPXDBGVJZCEX-UHFFFAOYSA-N- Molecular formula
- C7H15F3O3SSi
- Average molar mass
- 264.34 g/mol
- Monoisotopic mass
- 264.04632653
Names & identifiers
- Preferred name
- Triethylsilyl trifluoromethanesulphonate
- IUPAC
- triethylsilyl trifluoromethanesulfonate
- English name
- Triethylsilyl trifluoromethanesulfonate
- Molecular formula
- C7H15F3O3SSi
- Molecular weight
- 264.34
Names & synonyms
79271-56-0Triethylsilyl trifluoromethanesulphonateEINECS 279-124-4DTXSID00229597RefChem:899556DTXCID50152088279-124-4Triethylsilyl trifluoromethanesulfonateTriethylsilyl TriflatetriethylsilyltrifluoromethanesulfonateMFCD00000407Trifluoromethanesulfonic Acid Triethylsilyl Ester
Show more names
TES-OTFDKSI108DKSI136DKFELEX0305TESOTf 97%TES TRIFLATETriethyl(trifluoromesyloxy)silaneTriethylsilyl trifluoromethanesulfote
Methanesulfonic acid, trifluoro-, triethylsilyl esterS17625TESOTfEt3SiOTfTriethylsilyltriflateSCHEMBL36993STMPXDBGVJZCEX-UHFFFAOYSA-CS-B0887
Database identifiers
- CAS
79271-56-0- PubChem CID
- 2733308
- DTXSID
DTXSID00229597- EC Number
- 279-124-4
- Nikkaji
Properties
Computed structural properties
- Topological polar surface area
- 51.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 281
Physicochemical properties
- Boiling point
- 85 · 85-86 °C/12 mmHg (lit.)
- Density
- 1.169 g/mL · 1.169 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.389(lit.)
- Flash point
- 162 °F · 162 °F
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 2 Cl2 · Triethylsilyl Trifluoromethanesulfonate is readily sol hydrocarbons, dialkyl ethers, halogenated solvents. CH2Cl2 is employed most commonly. Reactions in 1,2-dichloroethane proceed faster than those in CCl4 or Et2O. Protic solvents and THF react with trialkylsilyl triflates and are therefore not suitable.
- form
- Fuming Liquid
- Specific Gravity
- 1.169 · 1.169
- color
- Clear colorless to light brown
- Water Solubility
- Miscible with dichloromethane, hydrocarbons, dialkyl ethers and halogenated solvents. Immiscible with water.
- Sensitive
- Moisture Sensitive
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- BRN
- 3590541 · 3590541
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Corr. 1 (100%)
Safety data
- F
- 10-21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- No
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29319090
- risk_code
- 34-14
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C,F
- hazard_note
- Corrosive/Flammable
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314
Chemistry & industry
Applications
UsesTriethylsilyl trifluoromethanesulfonate acts as a silylating agent. It is also useful as a Lewis acid catalyst. Further, it reacts with 1-diazo-3,3-dimethyl-butan-2-one to prepare 1-diazo-3,3-dimethyl-1-(triethylsilyl)-2-butanone.
UsesTriethylsilyl Trifluoromethanesulfonate can be used as potent silylating agent and as Lewis acid catalyst. Triethylsilyl ethers are generally more stable towards hydrolysis than are trimethylsilyl ethers, and consequently the Et3Si moiety has gained increasing use as a protecting group for alcohols. However, since it is often difficult to silylate sterically hindered hydroxyl groups using Et3SiCl, triethylsilyl perchlorate and triethylsilyl triflate (Et3SiOTf) were introduced to overcome this problem. Jefford has reported that condensation reactions of 2-trimethylsiloxyfuran with aldehydes can be catalyzed by Et3SiOTf to give mainly the threo addition product (eq 8).
Preparation methods
PreparationTriethylsilyl Trifluoromethanesulfonate can be prepared by reacting chlorotriethylsilane with trifluoromethanesulfonic acid followed by distillation.
Upstream & downstream products
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司
Related reactions
53 records
Compound notes
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