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Sigma-Aldrich

1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one

≥98.0% (AT)

Synonym(s):

1-{[Tris-(1-methylethyl)silyl]ethynyl]}-1,2-benziodoxol-3(1H)-one, TIPS-EBX

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About This Item

Empirical Formula (Hill Notation):
C18H25IO2Si
CAS Number:
181934-30-5
Molecular Weight:
428.38
MDL number:
MFCD18632570
UNSPSC Code:
12352005
PubChem Substance ID:
329764394
NACRES:
NA.22

assay

≥98.0% (AT)

form

crystals

reaction suitability

reaction type: C-C Bond Formation

SMILES string

CC(C)[Si](C#C[I]1OC(=O)c2ccccc12)(C(C)C)C(C)C

InChI

1S/C18H25IO2Si/c1-13(2)22(14(3)4,15(5)6)12-11-19-17-10-8-7-9-16(17)18(20)21-19/h7-10,13-15H,1-6H3

InChI key

NTHGHMCOPNSZIR-UHFFFAOYSA-N

Application

Introduction of silylacetylenes

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Direct alkynylation of indole and pyrrole heterocycles.
Jonathan P Brand et al.
Angewandte Chemie (International ed. in English), 48(49), 9346-9349 (2009-11-07)
Direct alkynylation of thiophenes: cooperative activation of TIPS-EBX with gold and Brønsted acids.
Jonathan P Brand et al.
Angewandte Chemie (International ed. in English), 49(40), 7304-7307 (2010-08-24)
Stefano Nicolai et al.
Organic letters, 12(2), 384-387 (2009-12-17)
The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority

Related Content

Waser Group – Professor Product Portal

The Waser laboratory is working on the development of non-conventional bond disconnections using the unique properties of hypervalent iodine reagents. In particular, they discovered the exceptional properties of 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) for electrophilic alkynylation.

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