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728365

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

728365-VAR:
728365-BULK:
728365-250MG:4548173999180
728365-1G:4548173999173

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC0627V
BCBD0674V
BCBD0674

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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
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)
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)

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