2-Bromo-5-phenylthiazole

Name: 2-Bromo-5-phenylthiazole
Brand: ChemScene
Availability: InStock
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CAS No. 133311-51-0
Cat. No. CS-0020038
Purity≥95%
MDL No.MFCD11109488

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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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Structure of 133311-51-0

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General Information

CAS No. 133311-51-0
Cat. No. CS-0020038
Purity ≥95%
MDL No. MFCD11109488
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₆BrNS
Molecular Weight None
Synonym(s) 2-Bromo-5-phenyl-1,3-thiazole
SMILES BrC1=NC=C(C2=CC=CC=C2)S1

Description

2-Bromo-5-phenylthiazole is a bench-stable heterocyclic building block featuring a bromine atom at the 2-position and a phenyl group at the 5-position, enabling efficient cross-coupling reactions. The electron-deficient thiazole core facilitates palladium-catalyzed transformations, while the para-substituted phenyl moiety enhances solubility and reactivity in synthetic sequences. This compound serves as a key intermediate in medicinal chemistry and materials science applications.

Application

2-Bromo-5-phenylthiazole serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl and extended π-conjugated systems. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the phenylthiazole core offers enhanced stability and functional group tolerance. Its bench-stable crystalline form facilitates handling and purification, making it ideal for medicinal chemistry campaigns and materials science applications requiring precise molecular architecture.

Synthesis

Route1
- In-stock
  
  39136-63-5
- In-stock
  
  7758-99-8
- ~99%
- In-stock
  
  133311-51-0
References
- JANSSEN PHARMACEUTICA N.V. Patent: EP398425 A1, 1990 ;
Route2
- In-stock
  
  3034-48-8
- 71-43-2
- ~12%
- In-stock
  
  133311-51-0
References
- D'Auria, Maurizio; Distefano, Claudio; D'Onofrio, Franco; Mauriello, Giacomo; Racioppi, Rocco Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 20 p. 3513 - 3518

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 : P260-P280-P302+P352-P304+P340

Quality Control

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Computational Chemistry Data

TPSA 12.89
LogP 3.5726
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Thiazole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-5-phenylthiazole

CAS No. 133311-51-0

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