Skip to Content
Merck
CN
All Photos(2)

Documents

728365

Sigma-Aldrich

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

≥98.0% (AT)

Sign Into View Organizational & Contract Pricing
All Photos(2)
Synonym(s):
1-{[Tris-(1-methylethyl)silyl]ethynyl]}-1,2-benziodoxol-3(1H)-one, TIPS-EBX
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

Related Categories

Application

Introduction of silylacetylenes

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

Hazard Classifications

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

Target Organs

Respiratory system

WGK

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service