ChemicalBook > CAS DataBase List > TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

Product Name
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
CAS No.
80522-42-5
Chemical Name
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
Synonyms
TIPS-OTF;TRIISOPROPYLSILYL TRIFLATE;Triisopropylsilyl;(i-Pr)3SiOTf;TIPS TRIFLATE;Triisopropyl trifluoromethane sulfonate;TRIISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE;SILANE IP3-TRIFLATE;WACKER SILANE IP3-TRIFLATE;TRIISOPROPYLSILYL TRIFLUOROMETHANESULFOTE
CBNumber
CB5189874
Molecular Formula
C10H21F3O3SSi
Formula Weight
306.42
MOL File
80522-42-5.mol
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TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE Property

Boiling point:
45-46 °C/0.03 mmHg
Density 
1.14 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.415(lit.)
Flash point:
213 °F
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Miscible with chloroform and ethyl acetate.
form 
Liquid
Specific Gravity
1.14
color 
Clear light brown to orange-brown
Sensitive 
Moisture Sensitive
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
BRN 
3591541
InChI
InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
InChIKey
LHJCZOXMCGQVDQ-UHFFFAOYSA-N
SMILES
C(F)(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O
CAS DataBase Reference
80522-42-5(CAS DataBase Reference)
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Safety

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
26-36/37/39-45-28A-27
RIDADR 
UN 3265 8/PG 2
WGK Germany 
3
F 
3-10-21
TSCA 
No
HazardClass 
8
PackingGroup 
II
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
248460
Product name
Triisopropylsilyl trifluoromethanesulfonate
Purity
97%
Packaging
10g
Price
$145
Updated
2024/03/01
Sigma-Aldrich
Product number
248460
Product name
Triisopropylsilyl trifluoromethanesulfonate
Purity
97%
Packaging
50g
Price
$237.6
Updated
2024/03/01
TCI Chemical
Product number
T1588
Product name
Triisopropylsilyl Trifluoromethanesulfonate
Purity
>98.0%(T)
Packaging
5g
Price
$28
Updated
2024/03/01
TCI Chemical
Product number
T1588
Product name
Triisopropylsilyl Trifluoromethanesulfonate
Purity
>98.0%(T)
Packaging
25g
Price
$102
Updated
2024/03/01
Alfa Aesar
Product number
B21127
Product name
Triisopropylsilyl trifluoromethanesulfonate
Purity
97%
Packaging
5g
Price
$40.65
Updated
2024/03/01
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TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE Chemical Properties,Usage,Production

Chemical Properties

clear light brown to orange-brown liquid

Physical properties

Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173 g cm?3.

Uses

Triisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers and converting ketones and lactones into their enol silyl ethers; protection of terminal alkynes; promoting conjugate addition of alkynylzinc compounds to α,β-enones; preparation of (triisopropylsilyl)diazomethane, participating in the following (but not limited to) reactions: Silylation of Alcohols, Formations of Enol Silyl Ethers, Alkynyltriisopropylsilanes, Conjugate Addition of Alkynylzinc Bromides, (Triisopropylsilyl)diazomethane, Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines, TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions, Benzannulation Using Triisopropylsilyl Vinyl Ketenes, Cyclization of 1-Silyloxy-1,5-diynes, Desymmetrization of Tartaric Acid Esters etc.

Uses

Triisopropylsilyl trifluoromethanesulfonate is used as a reagent for the introduction of triisopropylsilyl(TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.

Preparation

To 38.2 g (0.242 mol) of triisopropylsilane at 0°C under argon is added 23.8 mL (0.266 mol) of trifluoromethanesulfonic acid dropwise. The solution is stirred at 22°C for 16 h, at which time no further hydrogen gas evolves (removed through a bubbler). The resulting product is distilled through a 30-cm vacuum jacketed Vigreux column under reduced pressure: 71.7 g (97% yield) of TIPS triflate; bp 83–87°C/1.7 mmHg.

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE Preparation Products And Raw materials

Raw materials

Preparation Products

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TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE Suppliers

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View Lastest Price from TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Triisopropylsilyl trifluoromethanesulfonate 80522-42-5
Price
US $1.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20Tons
Release date
2020-01-13
Hebei Mojin Biotechnology Co., Ltd
Product
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 80522-42-5
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-30
LY Global chemicals co.,ltd .
Product
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 80522-42-5
Price
US $0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1000KG
Release date
2023-03-09

80522-42-5, TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATERelated Search:

Triethylsilane TRIETHYL 2-PHOSPHONOBUTYRATE Triethyloxonium tetrafluoroborate FLUOROTRIETHYLSILANE TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE Chlorotriethylsilane Sodium triacetoxyborohydride acetic acid, triethoxy-, ethyl ester triisopropylsilyl Methacrylate Triethylamine trihydrofluoride Triisopropylsilyl chloride Trimethoxysilane TRIFLUOROMETHANESULFONIC ACID DIETHYLISOPROPYLSILYL ESTER TrimethylSilyl Trifluoromethanesulfonate TRIETHYLSILANOL TRIMETHYLSILYL METHANESULFONATE Triisopropylsilane Triethylsilyl trifluoromethanesulfonate

  • Triisopropyl(trifluoromethylsulfonyloxy)silane
  • Triisopropylsilyl-trifluoromethanesulfonate,97%
  • Triisopropylsilyl
  • Triisopropylsilyl Triflate Trifluoromethanesulfonic Acid Triisopropylsilyl Ester
  • Triisopropyl trifluoromethane sulfonate
  • Triisopropylsilyl trifluoromethanesulfonate ,98%
  • (i-Pr)3SiOTf
  • Triisopropylsilyl-trifluoroMethanesulfonate, 97% 10GR
  • RIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
  • 1,1,1-TrifluoroMethanesulfonic Acid Tris(1-Methylethyl)silyl Ester
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULFOTE
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE, 97%TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE, 97%TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE, 97%
  • TRI ISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE 98%
  • SILANE IP3-TRIFLATE
  • TIPS-OTF
  • TIPS TRIFLATE
  • TRIFLUOROMETHANESULFONIC ACID TRIISOPROPYLSILYL ESTER
  • TRIISOPROPYLSILYL TRIFLATE
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE
  • WACKER SILANE IP3-TRIFLATE
  • TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate
  • TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate, Wacker Silane IP3-triflate
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 97%
  • Trifluormethansulfons?ure-tris(1-methylethyl)-silylester
  • Methanesulfonic acid, 1,1,1-trifluoro-, tris(1-methylethyl)silyl ester
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE ISO 9001：2015 REACH
  • 80522-42-5 TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
  • tri(propan-2-yl)silyl trifluoromethanesulfonate
  • TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE TIPS triflate, Triisopropylsilyl triflate
  • 80522-42-5
  • C10H21F3O3SSi
  • CF3SO3SiCHCH323
  • Synthetic Reagents
  • Silicon-Based
  • Protecting and Derivatizing Reagents
  • Protection and Derivatization
  • Silyl Esters
  • Protection & Derivatization Reagents (for Synthesis)
  • Silicon Compounds (for Synthesis)
  • Si (Classes of Silicon Compounds)
  • Si-O Compounds
  • Protection & Derivatization Reagents (for Synthesis)
  • Si (Classes of Silicon Compounds)
  • Silicon Compounds (for Synthesis)
  • Silyl Esters
  • Si-O Compounds
  • Synthetic Organic Chemistry