1-((Trimethylsilyl)ethynyl)-1l3-benzo[d][1,2]iodaoxol-3(1H)-one

Name: 1-((Trimethylsilyl)ethynyl)-1l3-benzo[d][1,2]iodaoxol-3(1H)-one
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CAS No. 181934-29-2
Cat. No. CS-0129628
Purity≥95%
MDL No.None

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1-((Trimethylsilyl)ethynyl)-1l3-benzo[d][1,2]iodaoxol-3(1H)-one|CS-0129628

Structure of 181934-29-2

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General Information

CAS No. 181934-29-2
Cat. No. CS-0129628
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₃IO₂Si
Molecular Weight 344.22
Synonym(s) 1-[(Trimethylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one
SMILES O=C1OI(C#C[Si](C)(C)C)C2=CC=CC=C21

Description

1-((Trimethylsilyl)ethynyl)-1,3-benzo[d][1,2]iodaoxol-3(1H)-one features a robust trimethylsilyl-protected alkyne handle paired with a reactive iodo-containing heterocycle. This combination enables stable storage and efficient coupling in late-stage functionalization workflows. The silyl group ensures moisture tolerance, while the iodine moiety facilitates palladium-catalyzed cross-coupling reactions under mild conditions.

Application

1-((Trimethylsilyl)ethynyl)-1,3-benzo[d][1,2]iodaoxol-3(1H)-one serves as a stable, bench-ready building block for the synthesis of complex heterocycles and functionalized aryl systems. The trimethylsilyl-protected alkyne enables efficient Sonogashira coupling reactions under mild conditions, while the iodo-oxolone scaffold provides a versatile platform for further derivatization. Its compatibility with diverse functional groups and ease of purification make it well-suited for iterative synthetic strategies in medicinal chemistry and materials science applications.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P280-P302+P352-P362

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Computational Chemistry Data

TPSA 26.3
LogP 3.2863
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Organosilicon compounds

Material Science Organic-Inorganic Hybrid Materials A silane coupling agent

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Chemical Synthesis Synthetic Reagents Hypervalent Iodine Compounds

Chemical Synthesis Organometallic Reagents Organosilicon Ethynylsilanes

Chemical Synthesis Synthetic Reagents Oxidation Hypervalent Iodine

Chemical Synthesis Synthetic Reagents C-X(Non-Halogen) Bond Formation Ethynylation

Key Words

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1-((Trimethylsilyl)ethynyl)-1l3-benzo[d][1,2]iodaoxol-3(1H)-one

CAS No. 181934-29-2

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