5'-Bromo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

Name: 5'-Bromo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one
Brand: ChemScene
Availability: InStock
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CAS No. 875071-97-9
Cat. No. CS-0050664
Purity≥95%
MDL No.MFCD13195328

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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5'-Bromo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one|CS-0050664

Structure of 875071-97-9

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General Information

CAS No. 875071-97-9
Cat. No. CS-0050664
Purity ≥95%
MDL No. MFCD13195328
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₈BrNO
Molecular Weight 238.08
Synonym(s) 5'-Bromospiro[cyclopropane-1,3'-indolin]-2'-one
SMILES BrC1=CC2=C(NC(=O)C22CC2)C=C1

Description

This spirocyclic indole derivative features a brominated cyclopropane ring fused to an indole core, enabling direct functionalization in C–H activation and cross-coupling reactions. The electron-deficient cyclopropane enhances reactivity in transition-metal catalyzed processes, while the ketone group provides a handle for further derivatization. Bench-stable and moisture-tolerant, it streamlines access to complex heterocycles in synthetic and medicinal chemistry.

Application

5'-Bromo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one serves as a versatile building block for the construction of spirocyclic indole scaffolds prevalent in bioactive molecules. The bromine substituent enables palladium-catalyzed cross-coupling reactions, while the cyclopropane-indole fusion provides structural rigidity and enhanced metabolic stability. Its bench-stable nature and compatibility with standard synthetic protocols facilitate efficient access to complex heterocyclic architectures in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  13861-75-1
- ~99%
- In-stock
  
  875071-97-9
References
- Wyeth Patent: US2006/30615 A1, 2006 ; Location in patent: Page/Page column 9 ;
Route2
- In-stock
  
  59-48-3
- ~%
- In-stock
  
  875071-97-9
References
- Fensome, Andrew; Bender, Reinhold; Cohen, Jeffrey; Collins, Mark A; Mackner, Valerie A; Miller, Lori L; Ullrich, John W; Winneker, Richard; Wrobel, Jay; Zhang, Puwen; Zhang, Zhiming; Zhu, Yuan Bioorganic and medicinal chemistry letters, 2002 , vol. 12, # 23 p. 3487 - 3490

Safety Information

Download SDS

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

Quality Control

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Computational Chemistry Data

TPSA 29.1
LogP 2.4328
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Indolin compounds

Building Blocks Skeleton Fatty ring compounds Cyclopropane compounds

Key Words

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5'-Bromo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

CAS No. 875071-97-9

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