2-Bromo-6-fluoroquinoline

Name: 2-Bromo-6-fluoroquinoline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 159870-91-4
Cat. No. CS-0156748
Molecule weight226.05
Purity≥97%
MDL No.MFCD09261122

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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 159870-91-4

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General Information

CAS No. 159870-91-4
Cat. No. CS-0156748
Purity ≥97%
MDL No. MFCD09261122
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅BrFN
Molecular Weight 226.05
Synonym(s) None
SMILES C1=CC(=NC2=CC=C(C=C12)F)Br

Description

2-Bromo-6-fluoroquinoline is a heterocyclic building block featuring bromine and fluorine substituents at adjacent positions on the quinoline core. This combination imparts enhanced electron deficiency and directional reactivity, enabling efficient coupling in cross-coupling protocols. The molecule exhibits robust stability under standard reaction conditions and facilitates access to complex nitrogen-containing architectures in medicinal chemistry and materials science applications.

Application

2-Bromo-6-fluoroquinoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogen reactivity. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the fluorine substituent enhances metabolic stability and modulates electronic properties. Its bench-stable nature and compatibility with diverse functional groups make it well-suited for constructing complex heterocyclic scaffolds in API development.

Synthesis

Route1
- 2338-74-1
- ~70%
- In-stock
  
  159870-91-4
References
- Wengryniuk, Sarah E.; Weickgenannt, Andreas; Reiher, Christopher; Strotman, Neil A.; Chen, Ke; Eastgate, Martin D.; Baran, Phil S. Organic Letters, 2013 , vol. 15, # 4 p. 792 - 795
Route2
- In-stock
  
  396-30-5
- ~%
- In-stock
  
  159870-91-4
References
- Wengryniuk, Sarah E.; Weickgenannt, Andreas; Reiher, Christopher; Strotman, Neil A.; Chen, Ke; Eastgate, Martin D.; Baran, Phil S. Organic Letters, 2013 , vol. 15, # 4 p. 792 - 795

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 12.89
LogP 3.1364
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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2-Bromo-6-fluoroquinoline

CAS No. 159870-91-4

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