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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;DKFELEX0272;SILANE IP3-TRIFLATE;WACKER SILANE IP3-TRIFLATE
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
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.

Reactivity Profile

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).

References

[1] Rücker, C. “1,3‐Bis(triisopropylsilyl)propyne.” 2001. 0.
[2] Fumihiko Yoshimura. “Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ.” Synlett 29 1 (2017): 1816–1820.

Triisopropylsilyl Trifluoromethanesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products

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Triisopropylsilyl Trifluoromethanesulfonate Suppliers

Shanghai chuqing Organosilane technology ltd
Tel
021-61530618
Fax
86-21-51714575
Email
sales@chuqingtech.com
Country
China
ProdList
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55
SHANG FLUORO
Tel
021-65170832 15601903708
Email
qinba_1@163.com
Country
China
ProdList
374
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60
Yangzhou Sanyou Synthesis Chemical Co., Ltd
Tel
0514-85083918 13056321938
Email
sales@upkind.com
Country
China
ProdList
41
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
New Energy Chemicals
Tel
0515-82159088 13770142076
Fax
86-0515-8215909
Email
twl@njuchem.com
Country
China
ProdList
213
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65
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8418
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55
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
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View Lastest Price from Triisopropylsilyl Trifluoromethanesulfonate manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 80522-42-5
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100 mt
Release date
2024-11-12
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:


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  • 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