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248460

Sigma-Aldrich

Triisopropylsilyl trifluoromethanesulfonate

97%

Synonym(s):

TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate

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About This Item

Linear Formula:
CF3SO3Si[CH(CH3)2]3
CAS Number:
80522-42-5
Molecular Weight:
306.42
Beilstein:
3591541
MDL number:
MFCD00009913
UNSPSC Code:
12352001
PubChem Substance ID:
24854929
NACRES:
NA.22

Quality Level

100

Assay

97%

refractive index

n20/D 1.415 (lit.)

bp

45-46 °C/0.03 mmHg

density

1.14 g/mL at 25 °C (lit.)

functional group

fluoro
triflate

SMILES string

CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C

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

InChI key

LHJCZOXMCGQVDQ-UHFFFAOYSA-N

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Application

Used to prepare silyloxy acetylenes from lithium acetylides; the silyloxy acetylenes were then employed in protic acid-promoted cyclizations of arenes, alkynes and olefins.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

217.4 °F - closed cup

Flash Point(C)

103 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK4260
SHBJ8919
SHBD5403V
SHBC1085V
45096AMV

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Tetrahedron, 62, 11371-11371 (2006)
Greene, T.W. Wuts, P.G.M.
Protective Groups in Organic Synthesis, 74-74 (1991)
Ryunosuke Kuriki et al.
Dalton transactions (Cambridge, England : 2003), 49(35), 12234-12241 (2020-08-28)
New types of diaryloxystannylenes and -plumbylenes have been synthesized and structurally characterized. Lappert's diaminostannylene and -plumbylene E[N(SiMe3)2]2 (E = Sn, Pb) react with 1,3-diethers of tetrathiacalix[4]arene bearing benzyl or SiiPr3 groups to give the corresponding diaryloxystannylenes and -plumbylenes embedded in
Synlett, 435-435 (1993)

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