3-Bromo-1-(triisopropylsilyl)-1H-indole

Name: 3-Bromo-1-(triisopropylsilyl)-1H-indole
Brand: ChemScene
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CAS No. 148249-36-9
Cat. No. CS-0131941
Purity≥97%
MDL No.MFCD02093441

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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3-Bromo-1-(triisopropylsilyl)-1H-indole|CS-0131941

Structure of 148249-36-9

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General Information

CAS No. 148249-36-9
Cat. No. CS-0131941
Purity ≥97%
MDL No. MFCD02093441
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₇H₂₆BrNSi
Molecular Weight 352.38
Synonym(s) 3-Bromo-1-(triisopropylsilyl)indole
SMILES CC([Si](N1C=C(Br)C2=C1C=CC=C2)(C(C)C)C(C)C)C

Description

3-Bromo-1-(triisopropylsilyl)-1H-indole features a brominated indole core stabilized by a bulky triisopropylsilyl group, enhancing its shelf stability and resistance to protodesilylation. This derivative enables direct functionalization in late-stage C–H arylation and cross-coupling reactions under mild conditions. The silyl moiety facilitates protection of the indole nitrogen while maintaining compatibility with palladium-catalyzed transformations.

Application

3-Bromo-1-(triisopropylsilyl)-1H-indole serves as a versatile building block for indole-based scaffolds in medicinal chemistry and materials science. The triisopropylsilyl group provides robust protection of the indole nitrogen, enabling orthogonal functionalization and enhanced stability during synthetic manipulations. The bromo substituent at C3 facilitates palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, under standard conditions. Its bench-stable nature and compatibility with diverse reaction environments make it well-suited for multi-step synthesis and scale-up 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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Computational Chemistry Data

TPSA 4.93
LogP 6.4274
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Material Science Organic-Inorganic Hybrid Materials A silane coupling agent

Key Words

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3-Bromo-1-(triisopropylsilyl)-1H-indole

CAS No. 148249-36-9

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