5-Bromo-8-methylquinoline

Name: 5-Bromo-8-methylquinoline
Brand: ChemScene
Availability: InStock
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CAS No. 74316-55-5
Cat. No. CS-0131203
Purity≥96%
MDL No.MFCD04966995

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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 74316-55-5

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General Information

CAS No. 74316-55-5
Cat. No. CS-0131203
Purity ≥96%
MDL No. MFCD04966995
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₈BrN
Molecular Weight 222.08
Synonym(s) 5-BROMO-8-METHYL-QUINOLINE
SMILES CC1=C2N=CC=CC2=C(Br)C=C1

Description

5-Bromo-8-methylquinoline is a heterocyclic scaffold featuring a bromine substituent at the 5-position and a methyl group at the 8-position on the quinoline core. This configuration imparts enhanced electron-withdrawing character and steric profile, enabling efficient coupling in palladium-catalyzed transformations. The molecule exhibits good stability under standard reaction conditions and facilitates access to complex functionalized architectures in medicinal chemistry and materials science applications.

Application

5-Bromo-8-methylquinoline serves as a versatile building block in medicinal chemistry and catalytic synthesis, enabling direct functionalization at the quinoline core. The bromine atom facilitates palladium-catalyzed cross-coupling reactions, while the methyl group enhances solubility and modulates electronic properties. Its bench-stable nature and compatibility with standard reaction conditions make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

Route1
- 611-32-5
- ~85%
- In-stock
  
  74316-55-5
References
- Evans, Paul; Hogg, Paul; Grigg, Ronald; Nurnabi, Mohamed; Hinsley, Joanne; Sridharan, Visuvanathar; Suganthan, Selvaratnam; Korn, Stewart; Collard, Simon; Muir, Jane E. Tetrahedron, 2005 , vol. 61, # 41 p. 9696 - 9704
Route2
- 611-32-5
- ~58%
- In-stock
  
  74316-55-5
- 98786-47-1
References
- Chemistry of Heterocyclic Compounds (New York, NY, United States), , vol. 24, # 8 p. 892 - 897 Khimiya Geterotsiklicheskikh Soedinenii, , # 8 p. 1084 - 1090

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 3.30572
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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5-Bromo-8-methylquinoline

CAS No. 74316-55-5

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