2-Bromo-4H,5H,6H-cyclopenta[d][1,3]thiazole

Name: 2-Bromo-4H,5H,6H-cyclopenta[d][1,3]thiazole
Brand: ChemScene
Availability: InStock
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CAS No. 1080642-17-6
Cat. No. CS-0076396
Purity≥98%
MDL No.None

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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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2-Bromo-4H,5H,6H-cyclopenta[d][1,3]thiazole|CS-0076396

Structure of 1080642-17-6

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General Information

CAS No. 1080642-17-6
Cat. No. CS-0076396
Purity ≥98%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₆BrNS
Molecular Weight 204.09
Synonym(s) 2-Bromo-5,6-dihydro-4H-cyclopenta[d]thiazole
SMILES BrC(S1)=NC2=C1CCC2

Description

2-Bromo-4H,5H,6H-cyclopenta[d][1,3]thiazole is a heterocyclic bromide featuring a fused cyclopentathiazole core with defined stereochemistry. This bench-stable compound integrates readily into transition-metal-catalyzed coupling reactions due to its reactive C–Br bond and electron-deficient aromatic system. The molecule’s rigidity enhances regioselectivity in downstream functionalization, making it valuable for synthesizing bioactive scaffolds and advanced intermediates in medicinal chemistry and materials science.

Application

2-Bromo-4H,5H,6H-cyclopenta[d][1,3]thiazole serves as a versatile heterocyclic building block for medicinal chemistry and materials synthesis. The bromine substituent enables facile palladium-catalyzed cross-coupling reactions, facilitating the construction of biaryl and styryl architectures. Its fused thiazole core provides enhanced stability and defined electronic properties, while the cyclopentane fusion offers rigidity beneficial for conformational control in target molecule design.

Synthesis

Route1
- In-stock
  
  53051-97-1
- ~13%
- In-stock
  
  1080642-17-6
References
- LI, Wei; Li, Jianchang; Wu, Yuchuan; Wu, Junjun; Hotchandani, Rajeev; Tam, Steve Yikkai; Suhayl, Tarek; Sypek, Joseph P.; McFadyen, Iain Patent: US2010/227859 A1, 2010 ; Location in patent: Page/Page column 87 ; US 20100227859 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 12.89
LogP 2.3943
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Thiazole compounds

Key Words

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2-Bromo-4H,5H,6H-cyclopenta[d][1,3]thiazole

CAS No. 1080642-17-6

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